The structure is contained in the following publication(s):
Article ID: 494
Torzewska A, Kocharova NA, Maszewska A, Knirel YA, Rozalski A "Serological characterization of the O-specific polysaccharide of Providencia alcalifaciens O23" -
Archivum Immunologiae et Therapiae Experimentalis52(1) (2004) 43-49
INTRODUCTION: The genus Providencia belongs to the Enterobacteriaceae family and currently consists of five species: P. alcalifaciens, P. heimbachae, P. rettgerii, P. rustigianii and P. stuartii. The serological classification scheme of P. alcalifaciens, P. rustigianii and P. stuartii includes 63 O-serogroups and 30 H-serogroups. The O-antigenic specificity is defined by the structure of the O-antigen (O-specific polysaccharide--OPS), a part of the lipopolysaccharide (LPS, endotoxin), one of the major components of the outer membrane of gram-negative bacteria and an important virulence factor of these bacteria. Among the bacteria of the Enterobacteriaceae family, the genus Providencia is one of the least studied in respect to its LPS structure and antigenic specificity. Studies of the chemical structures and the serological specificity of the O-antigens aim at the elucidation of the molecular basis of the serological classification of Providencia sp. MATERIALS AND METHODS: LPS and alkali-treated LPS of P. alcalifaciens O23 and serologically related P. rustigianii O14, P. mirabilis O13 and P. myxofaciens as well as O-antiserum against P. alcalifaciens O23 were used. Serological characterization of P. alcalifaciens O23 O-specific polysaccharide was done by use enzyme immunosorbent assay (EIA), passive hemolysis test (PHT) as well as by inhibition and sodium deoxycholate polyacrylamide gel electrophoresis (DOC-PAGE) of LPS and Western blot. RESULTS AND CONCLUSIONS: The OPS of P. alcalifaciens, O23, contains an N-(D-glucuronoyl)-N-[(R)-1-carboxyethyl]-L-lysine residue (GlcAAlaLys). The LPS of P. alcalifaciens, O23, and other LPSs containing AlaLys from Providencia and Proteus strains were tested with rabbit anti-P. alcalifiaciens O23 serum. The serological data showed that a GlcAAlaLys-associated epitope plays a role as an antigenic determinant in the P. alcalifaciens O23 OPS and revealed the particular importance of glucuronic acid and the carboxyethyl group for the binding of O23-specific antibodies.
NCBI PubMed ID:15053232 Journal NLM ID:0114365 Publisher: Basel, Boston: Birkhaüser Correspondence: rozala@biol.uni.lodz.pl Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Institute of Microbiology and Immunology, University of Lodz, Lodz, Poland
Article ID: 867
Kocharova NA, Shcherbakova OV, Shashkov AS, Knirel YA, Kochetkov NK, Kholodkova EV, Stanislavsky ES "Structure of the O-specific polysaccharide of the bacterium Providencia alcalifaciens serogroup O23 containing a novel amide of D-glucuronic acid with Ne-(1-carboxyethyl)lysine" -
Biochemistry (Moscow)62 (1997) 501-508
An acidic O-specific polysaccharide was obtained by mild acid degradation of the lipopolysaccharide of the bacterium Providencia alcalifaciens O23 and found to contain D-glucose, D-galactose, 2-acetamido-2-deoxy-D-galactose, and N ε-(1-carboxyethyl)-N α-(D-glucuronoyl)lysine. On the basis of full and partial acid hydrolyses, selective solvolysis with anhydrous hydrogen fluoride, and 1H- and 13C NMR spectroscopy, including two-dimensional correlation spectroscopy (COSY), H-detected heteronuclear 1H, 13C multi-quantum coherence (HMQC), and rotating-frame nuclear Overhauser effect spectroscopy (ROESY), the following structure of the liner tetrasaccharide repeating unit of the polysaccharide was established [structure: see text]
NCBI PubMed ID:9275290 Journal NLM ID:0376536 Publisher: Nauka/Interperiodica Correspondence: knirel@ioc.ac.ru Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia Methods: partial acid hydrolysis, NMR, HF solvolysis, MS, borohydride reduction
Article ID: 869
Kocharova NA, Vinogradov EV, Borisova SA, Shashkov AS, Knirel YA "Identification of Ne-[(R)-1-carboxyethyl]-L-lysine in, and the complete structure of, the repeating unit of the O-specific polysaccharide of Providencia alcalifaciens O23" -
Carbohydrate Research309(1) (1998) 131-133
N ε-[(R)-1-Carboxyethyl]-L-lysine was released by acid hydrolysis from the O-specific polysaccharide of Providencia alcalifaciens O23 and identified by 1H and 13C NMR spectroscopy, GLC-MS after conversion to a di-N-acetylated dimethyl ester, and by comparison with the authentic sample. Solvolysis of the polysaccharide with anhydrous HF resulted in an amide of D-glucuronic acid with N ε-[(R)-1-carboxyethyl]-L-lysine. These and published data allowed the determination of the full structure of the repeating unit of the O-specific polysaccharide.
NCBI PubMed ID:9720244 Journal NLM ID:0043535 Publisher: Elsevier Correspondence: knirel@ioc.ac.ru Institutions: N.D.Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia Methods: NMR, HF solvolysis, MS
Article ID: 877
Kocharova NA, Zatonsky GV, Torzewska A, Macieja Z, Bystrova OV, Shashkov AS, Knirel YA, Rozalski A "Structure of the O-specific polysaccharide of Providencia rustigianii O14 containing Na-[(S)-1-carboxyethyl]-Ne-(D-galacturonoyl)-L-lysine" -
Carbohydrate Research338(9) (2003) 1009-1016
The O-specific polysaccharide of Providencia rustigianii O14 was obtained by mild acid degradation of the LPS and studied by chemical methods and NMR spectroscopy, including 2D 1H,(1)H COSY, TOCSY, NOESY, and 1H,(13)C HSQC experiments. The polysaccharide was found to contain N(ε)-[(S)-1-carboxyethyl]-N(α)-(D-galacturonoyl)-L-lysine ('alaninolysine', 2S,8S-AlaLys). The amino acid component was isolated by acid hydrolysis and identified by 13C NMR spectroscopy and specific optical rotation, using synthetic diastereomers for comparison. The following structure of the trisaccharide repeating unit of the polysaccharide was established: . Anti-P. rustigianii O14 serum was found to cross-react with O-specific polysaccharides of Providencia and Proteus strains that contains amides of uronic acid with N(ε)-[(R)-1-carboxyethyl]-L-lysine and L-lysine.
structure, O-specific polysaccharide, Providencia alcalifaciens, Alaninolysine, bacterial polysaccharide structures, Nα-(D-galacturonoyl)-Nε-[(S)-1-carboxyethyl)-L-lysine, Providencia rustigianii, Providencia rustigianii; published polymerization frame was shifted for conformity with other records.
NCBI PubMed ID:12681927 Publication DOI:10.1016/S0008-6215(03)00019-3 Journal NLM ID:0043535 Publisher: Elsevier Correspondence: rozala@biol.uni.lodz.pl Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospekt 47, 119991 Moscow, GSP-1, Russia, Department of Immunobiology of Bacteria, Institute of Microbiology and Immunology, University of Lodz, Banacha 12/16, 90-237 Lodz, Poland Methods: methylation, NMR, acid hydrolysis
Article ID: 4329
Knirel YA "Structure of O-antigens" -
Book: Bacterial lipopolysaccharides: Structure, chemical synthesis, biogenesis and interaction with host cells (2011) Chapter 3, 41-115
The lipopolysaccharide (LPS) is the major constituent of the outer leaflet of the outer membrane of Gram-negative bacteria. Its lipid A moiety is embedded in the membrane and serves as an anchor for the rest of the LPS molecule. The outermost repetitive glycan region of the LPS is linked to the lipid A through a core oligosaccharide (OS), and is designated as the O-specific polysaccharide (O-polysaccharide, OPS) or O-antigen. The O-antigen is the most variable portion of the LPS and provides serological specificity, which is used for bacterial serotyping. The OPS also provides protection to the microorganisms from host defenses such as complement mediated killing and phagocytosis, and is involved in interactions of bacteria with plants and bacteriophages. Studies of the OPSs ranging from the elucidation of their chemical structures and conformations to their biological and physico-chemical properties help improving classification schemes of Gram-negative bacteria. Furthermore, these studies contributed to a better understanding of the mechanisms of pathogenesis of infectious diseases, as well as provided information to develop novel vaccines and diagnostic reagents.
Lipopolysaccharide, synthesis, lipopolysaccharides, structure, Bacterial, host, O-antigen, O antigen, cell, O antigens, O-antigens, chemical, interaction, cells, PDF, chemical synthesis, biogenesis
Publication DOI:10.1007/978-3-7091-0733-1_3 Publisher: Springer Correspondence: knirel@ioc.ac.ru Editors: Knirel YA, Valvano MA Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
Article ID: 4589
Ovchinnikova OG, Rozalski A, Liu B, Knirel YA "O-Antigens of bacteria of the genus Providencia: structure, serology, genetics, and biosynthesis" -
Biochemistry (Moscow)78(7) (2013) 798-817
The genus Providencia consists of eight species of opportunistic pathogenic enterobacteria that can cause enteric diseases and urinary tract infections. The existing combined serological classification scheme of three species, P. alcalifaciens, P. stuartii, and P. rustigianii, is based on the specificity of O-antigens (O-polysaccharides) and comprises 63 O-serogroups. Differences between serogroups are related to polymorphism at a specific genome locus, the O-antigen gene cluster, responsible for O-antigen biosynthesis. This review presents data on structures of 36 O-antigens of Providencia, many of which contain unusual monosaccharides and non-carbohydrate components. The structural data correlate with the immunospecificity of the O-antigens and enable substantiation on a molecular level of serological relationships within the genus Providencia and between strains of Providencia and bacteria of the genera Proteus, Escherichia, and Salmonella. Peculiar features of the O-antigen gene cluster organization in 10 Providencia serogroups and biosynthetic pathways of nucleotide precursors of specific monosaccharide components of the O-antigens also are discussed.
NCBI PubMed ID:24010842 Publication DOI:10.1134/S0006297913070110 Journal NLM ID:0376536 Publisher: Nauka/Interperiodica Correspondence: olga.ovchinnikova@gmail.com Institutions: ND Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Department of Immunobiology of Bacteria, Institute of Microbiology, Biotechnology and Immunology, University of Lodz, PL 90-237 Lodz, Poland, TEDA School of Biological Sciences and Biotechnology, Nankai University, 23 Hongda Street, TEDA, 300457 Tianjin, P. R. China
Article ID: 4997
Hanske J, Schulze J, Aretz J, McBride R, Loll B, Schmidt H, Knirel Y, Rabsch W, Wahl MC, Paulson JC, Rademacher C "Bacterial polysaccharide specificity of the pattern recognition receptor Langerin is highly species dependent" -
Journal of Biological Chemistry292(3) (2017) 862-871
The recognition of pathogen surface polysaccharides by glycan-binding proteins is a cornerstone of innate host defense. Many members of the C-type lectin receptor family serve as pattern recognition receptors facilitating pathogen uptake, antigen processing, and immunomodulation. Despite the high evolutionary pressure in host-pathogen interactions, it is still widely assumed that genetic homology conveys similar specificities. Here, we investigate the ligand specificities of the human and murine forms of the myeloid C-type lectin receptor langerin for simple and complex ligands augmented by structural insight into murine langerin. Although the two homologs share the same three-dimensional structure and recognize simple ligands identically, a screening of more than 300 bacterial polysaccharides revealed highly diverging avidity and selectivity for larger and more complex glycans. Structural and evolutionary conservation analysis identified a highly variable surface adjacent to the canonic binding site, potentially forming a secondary site of interaction for large glycans.
NCBI PubMed ID:27903635 Publication DOI:10.1074/jbc.M116.751750 Journal NLM ID:2985121R Publisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology Correspondence: Christoph.Rademacher@mpikg.mpg.de Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Department of Biomolecular Systems, Max Planck Institute of Colloids and Interfaces, Potsdam 14424, Germany, Department of Biology, Chemistry, and Pharmacy, Freie Universitat Berlin, Berlin 14195, Germany, Department of Cell and Molecular Biology, Department of Immunology and Microbial Science and Department of Chemical Physiology, Scripps Research Institute, La Jolla, California 92037, Robert Koch Institute, Wernigerode Branch, National Reference Centre for Salmonellae and other Bacterial Enteric Pathogens, Wernigerode 38855, Germany Methods: X-ray, SDS-PAGE, genetic methods, STD NMR, cloning, crystallization, ITC, glycan array analysis, flow cytometry analysis
The structure is contained in the following publication(s):
Article ID: 494
Torzewska A, Kocharova NA, Maszewska A, Knirel YA, Rozalski A "Serological characterization of the O-specific polysaccharide of Providencia alcalifaciens O23" -
Archivum Immunologiae et Therapiae Experimentalis52(1) (2004) 43-49
INTRODUCTION: The genus Providencia belongs to the Enterobacteriaceae family and currently consists of five species: P. alcalifaciens, P. heimbachae, P. rettgerii, P. rustigianii and P. stuartii. The serological classification scheme of P. alcalifaciens, P. rustigianii and P. stuartii includes 63 O-serogroups and 30 H-serogroups. The O-antigenic specificity is defined by the structure of the O-antigen (O-specific polysaccharide--OPS), a part of the lipopolysaccharide (LPS, endotoxin), one of the major components of the outer membrane of gram-negative bacteria and an important virulence factor of these bacteria. Among the bacteria of the Enterobacteriaceae family, the genus Providencia is one of the least studied in respect to its LPS structure and antigenic specificity. Studies of the chemical structures and the serological specificity of the O-antigens aim at the elucidation of the molecular basis of the serological classification of Providencia sp. MATERIALS AND METHODS: LPS and alkali-treated LPS of P. alcalifaciens O23 and serologically related P. rustigianii O14, P. mirabilis O13 and P. myxofaciens as well as O-antiserum against P. alcalifaciens O23 were used. Serological characterization of P. alcalifaciens O23 O-specific polysaccharide was done by use enzyme immunosorbent assay (EIA), passive hemolysis test (PHT) as well as by inhibition and sodium deoxycholate polyacrylamide gel electrophoresis (DOC-PAGE) of LPS and Western blot. RESULTS AND CONCLUSIONS: The OPS of P. alcalifaciens, O23, contains an N-(D-glucuronoyl)-N-[(R)-1-carboxyethyl]-L-lysine residue (GlcAAlaLys). The LPS of P. alcalifaciens, O23, and other LPSs containing AlaLys from Providencia and Proteus strains were tested with rabbit anti-P. alcalifiaciens O23 serum. The serological data showed that a GlcAAlaLys-associated epitope plays a role as an antigenic determinant in the P. alcalifaciens O23 OPS and revealed the particular importance of glucuronic acid and the carboxyethyl group for the binding of O23-specific antibodies.
NCBI PubMed ID:15053232 Journal NLM ID:0114365 Publisher: Basel, Boston: Birkhaüser Correspondence: rozala@biol.uni.lodz.pl Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Institute of Microbiology and Immunology, University of Lodz, Lodz, Poland
Article ID: 877
Kocharova NA, Zatonsky GV, Torzewska A, Macieja Z, Bystrova OV, Shashkov AS, Knirel YA, Rozalski A "Structure of the O-specific polysaccharide of Providencia rustigianii O14 containing Na-[(S)-1-carboxyethyl]-Ne-(D-galacturonoyl)-L-lysine" -
Carbohydrate Research338(9) (2003) 1009-1016
The O-specific polysaccharide of Providencia rustigianii O14 was obtained by mild acid degradation of the LPS and studied by chemical methods and NMR spectroscopy, including 2D 1H,(1)H COSY, TOCSY, NOESY, and 1H,(13)C HSQC experiments. The polysaccharide was found to contain N(ε)-[(S)-1-carboxyethyl]-N(α)-(D-galacturonoyl)-L-lysine ('alaninolysine', 2S,8S-AlaLys). The amino acid component was isolated by acid hydrolysis and identified by 13C NMR spectroscopy and specific optical rotation, using synthetic diastereomers for comparison. The following structure of the trisaccharide repeating unit of the polysaccharide was established: . Anti-P. rustigianii O14 serum was found to cross-react with O-specific polysaccharides of Providencia and Proteus strains that contains amides of uronic acid with N(ε)-[(R)-1-carboxyethyl]-L-lysine and L-lysine.
structure, O-specific polysaccharide, Providencia alcalifaciens, Alaninolysine, bacterial polysaccharide structures, Nα-(D-galacturonoyl)-Nε-[(S)-1-carboxyethyl)-L-lysine, Providencia rustigianii, Providencia rustigianii; published polymerization frame was shifted for conformity with other records.
NCBI PubMed ID:12681927 Publication DOI:10.1016/S0008-6215(03)00019-3 Journal NLM ID:0043535 Publisher: Elsevier Correspondence: rozala@biol.uni.lodz.pl Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospekt 47, 119991 Moscow, GSP-1, Russia, Department of Immunobiology of Bacteria, Institute of Microbiology and Immunology, University of Lodz, Banacha 12/16, 90-237 Lodz, Poland Methods: methylation, NMR, acid hydrolysis
Article ID: 1241
Sidorczyk Z, Kondakova AN, Zych K, Senchenkova SN, Shashkov AS, Drzewiecka D, Knirel YA "Structure of the O-polysaccharide of Proteus myxofaciens. Classification of the bacterium into a new Proteus O-serogroup" -
European Journal of Biochemistry270(15) (2003) 3182-3188
The O-polysaccharide (O-antigen) was obtained from the lipopolysaccharide of Proteus myxofaciens, a Proteus strain producing copious amounts of slime, which was isolated from the gypsy moth larvae. The structure of the polysaccharide was studied by chemical analysis and 1H and 13C NMR spectroscopy, including 2D COSY, TOCSY, ROESY and H-detected 1H,13C HMQC experiments. It was found that the polysaccharide contains an amide of glucuronic acid (GlcA) with an unusual α-linked amino acid, Nε-[(R)-1-carboxyethyl]-l-lysine (2S,8R-alaninolysine, 2S,8R-AlaLys), and has a linear tetrasaccharide repeating unit of the following structure: This structure is unique among known bacterial polysaccharide structures. On the basis of these and serological data, it is proposed that P. myxofaciens be classified into a new Proteus serogroup, O60, of which this strain is the single representative. Structural and serological relatedness of P. myxofaciens to other AlaLys-containing O-antigens of Proteus and Providencia is discussed.
NCBI PubMed ID:12869193 Publication DOI:10.1046/j.1432-1033.2003.03698.x Journal NLM ID:0107600 Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies Correspondence: zsidor@biol.uni.lodz.pl Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Department of General Microbiology, Institute of Microbiology and Immunology, University of Lodz, Poland Methods: NMR-2D, NMR
Article ID: 3210
Kolodziejska K, Perepelov AV, Zablotni A, Drzewiecka D, Senchenkova SN, Zych K, Shashkov AS, Knirel YA, Sidorczyk Z "Structure of the glycerol phosphate-containing O-polysaccharides and serological studies of the lipopolysaccharides of Proteus mirabilis CCUG 10704 (OE) and Proteus vulgaris TG 103 classified into a new Proteus serogroup, O54" -
FEMS Immunology and Medical Microbiology47(2) (2006) 267-274
O-Polysaccharides were obtained from the lipopolysaccharides of Proteus mirabilis CCUG 10704 (OE) and Proteus vulgaris TG 103 and studied by chemical analyses and one- and two-dimensional (1)H and (13)C nuclear magnetic resonance spectroscopy, including rotating-frame nuclear Overhauser effect spectroscopy, H-detected (1)H,(13)C heteronuclear single-quantum spectroscopy and (1)H,(31)P heteronuclear multiple-quantum spectroscopy experiments. The Proteus mirabilis OE polysaccharide was found to have a trisaccharide repeating unit with a lateral glycerol phosphate group. The Proteus vulgaris TG 103 produces a similar O-polysaccharide, which differs in incomplete substitution with glycerol phosphate (c. 50% of the stoichiometric amount) and the presence of an O-acetyl group at position 6 of the 2-acetamido-2-deoxygalactose (GalNAc) residue. These structures are unique among the known bacterial polysaccharide structures. Based on the structural and serological data of the lipopolysaccharides, it is proposed to classify both strains studied into a new Proteus serogroup, O54, as two subgroups, O54a,54b and O54a,54c. The serological relatedness of the Proteus O54 and some other Proteus lipopolysaccharides is discussed.
NCBI PubMed ID:16831214 Publication DOI:10.1111/j.1574-695X.2006.00084.x Journal NLM ID:9315554 Publisher: Elsevier Correspondence: Zygmunt Sidorczyk Institutions: Department of General Microbiology, Institute of Microbiology and Immunology, University of Lodz, Lodz, Poland, N.D. Zelinsky Institute ofOrganic Chemistry, Russian Academy of Sciences, Moscow, Russia, Department of General Microbiology, Institute of Microbiology and Immunology, University of Lodz, Lodz, Poland. Methods: 13C NMR, 1H NMR, methylation, NMR-2D, GC-MS, HF solvolysis, chemical analysis, GLC, composition analysis, serological methods
Article ID: 4822
Palusiak A, Siwinska M, Zabłotni A "Proteus mirabilis RMS 203 as a new representative of the O13 Proteus serogroup" -
Acta Biochimica Polonica62(4) (2015) 691-695
The unique feature of some Proteus O-polysaccharides is occurrence of an amide of galacturonic acid with Nε-[(S/R)-1-Carboxyethyl]-l-lysine, GalA6(2S,8S/R-AlaLys). The results of the serological studies presented here, with reference to known O-antigens structures suggest that GalA6(2S,8S/R-AlaLys) or 2S,8R-AlaLys contribute to cross-reactions of O13 Proteus antisera, and Proteeae LPSs. It was also revealed that the Proteus mirabilis RMS 203 strain can be classified into the O13 serogroup, represented so far by two strains: Proteus mirabilis 26/57 and Proteus vulgaris 8344. The O13 LPS is a serologically important antigen with a fragment common to LPSs of different species in the Proteeae tribe.
NCBI PubMed ID:26645323 Publication DOI:10.18388/abp.2015_1108 Journal NLM ID:14520300R Publisher: Panstwowe Wydawnictwo Naukowe Correspondence: agatapal@biol.uni.lodz.pl Institutions: Department of General Microbiology, Institute of Microbiology, Biotechnology and Immunology, University of Łódź, Łódź, Poland Methods: serological methods
Article ID: 5760
Dobrochaeva K, Khasbiulina N, Shilova N, Antipova N, Obukhova P, Galanina O, Blixt O, Kunz H, Filatov A, Knirel Y, Le Pendu J, Khaidukov S, Bovin N "Specificity of human natural antibodies referred to as anti-Tn" -
Molecular Immunology120 (2020) 74-82
To understand the role of human natural IgM known as antibodies against the carbohydrate epitope Tn, the antibodies were isolated using GalNAcα-Sepharose affinity chromatography, and their specificity was profiled using microarrays (a glycan array printed with oligosaccharides and bacterial polysaccharides, as well as a glycopeptide array), flow cytometry, and inhibition ELISA. The antibodies bound a restricted number of GalNAcα-terminated oligosaccharides better than the parent monosaccharide, e.g., 6-O-Su-GalNAcα and GalNAcα1-3Galβ1-3(4)GlcNAcβ. The binding with several bacterial polysaccharides that have no structural resemblance to the affinity ligand GalNAcα was quite unexpected. Given that GalNAcα is considered the key fragment of the Tn antigen, it is surprising that these antibodies bind weakly GalNAcα-OSer and do not bind a wide variety of GalNAcα-OSer/Thr-containing mucin glycopeptides. At the same time, we have observed specific binding to cells having Tn-positive glycoproteins containing similar glycopeptide motifs in a conformationally rigid macromolecule. Thus, specific recognition of the Tn antigen apparently requires that the naturally occurring "anti-Tn" IgM recognize a complex epitope comprising the GalNAcα as an essential component and a fairly long amino acid sequence where the amino acids adjacent to GalNAcα do not contact the antibody paratope; i.e., the antibodies recognize a spatial epitope or a molecular pattern rather than a classical continuous sequence. In addition, we have not found any increase in the binding of natural antibodies when GalNAcα residues were clustered. These results may help in further development of anticancer vaccines based on synthetic Tn constructs.
NCBI PubMed ID:32087569 Publication DOI:10.1016/j.molimm.2020.02.005 Journal NLM ID:7905289 Publisher: Elsevier Correspondence: professorbovin@yandex.ru Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, 16/10 Miklukho-Maklaya, Moscow, Russian Federation, Semiotik LLC, 16/10 Miklukho-Maklaya, Moscow, Russian Federation, National Medical Research Center for Obstetrics, Gynecology and Perinatology Named after Academician V.I. Kulakov of the Ministry of Healthcare of Russian Federation, Moscow, Russian Federation, National Research University Higher School of Economics, Moscow, Russian Federation, Department of Chemistry, Chemical Biology, University of Copenhagen, Thorvaldsensvej 40, 1871 Frederiksberg C, Denmark, Institut Fur Organische Chemie, Johannes Gutenberg-Universitat Mainz, Duesbergweg 10-14, D-55128, Mainz, Germany, Institute of Immunology, Federal Medical-Biological Agency of Russia, Moscow, Russian Federation, University of Nantes, Inserm, U892 IRT UN, 8 Quai MonCousu, BP70721 Nantes, FR 44007, France Methods: ELISA, affinity chromatography, flow cytometry analysis, printed glycan array (PGA) analysis, FACS assay
The structure is contained in the following publication(s):
Article ID: 494
Torzewska A, Kocharova NA, Maszewska A, Knirel YA, Rozalski A "Serological characterization of the O-specific polysaccharide of Providencia alcalifaciens O23" -
Archivum Immunologiae et Therapiae Experimentalis52(1) (2004) 43-49
INTRODUCTION: The genus Providencia belongs to the Enterobacteriaceae family and currently consists of five species: P. alcalifaciens, P. heimbachae, P. rettgerii, P. rustigianii and P. stuartii. The serological classification scheme of P. alcalifaciens, P. rustigianii and P. stuartii includes 63 O-serogroups and 30 H-serogroups. The O-antigenic specificity is defined by the structure of the O-antigen (O-specific polysaccharide--OPS), a part of the lipopolysaccharide (LPS, endotoxin), one of the major components of the outer membrane of gram-negative bacteria and an important virulence factor of these bacteria. Among the bacteria of the Enterobacteriaceae family, the genus Providencia is one of the least studied in respect to its LPS structure and antigenic specificity. Studies of the chemical structures and the serological specificity of the O-antigens aim at the elucidation of the molecular basis of the serological classification of Providencia sp. MATERIALS AND METHODS: LPS and alkali-treated LPS of P. alcalifaciens O23 and serologically related P. rustigianii O14, P. mirabilis O13 and P. myxofaciens as well as O-antiserum against P. alcalifaciens O23 were used. Serological characterization of P. alcalifaciens O23 O-specific polysaccharide was done by use enzyme immunosorbent assay (EIA), passive hemolysis test (PHT) as well as by inhibition and sodium deoxycholate polyacrylamide gel electrophoresis (DOC-PAGE) of LPS and Western blot. RESULTS AND CONCLUSIONS: The OPS of P. alcalifaciens, O23, contains an N-(D-glucuronoyl)-N-[(R)-1-carboxyethyl]-L-lysine residue (GlcAAlaLys). The LPS of P. alcalifaciens, O23, and other LPSs containing AlaLys from Providencia and Proteus strains were tested with rabbit anti-P. alcalifiaciens O23 serum. The serological data showed that a GlcAAlaLys-associated epitope plays a role as an antigenic determinant in the P. alcalifaciens O23 OPS and revealed the particular importance of glucuronic acid and the carboxyethyl group for the binding of O23-specific antibodies.
NCBI PubMed ID:15053232 Journal NLM ID:0114365 Publisher: Basel, Boston: Birkhaüser Correspondence: rozala@biol.uni.lodz.pl Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Institute of Microbiology and Immunology, University of Lodz, Lodz, Poland
Article ID: 1091
Perepelov AV, Senchenkova SN, Cedzynski M, Ziolkowski A, Vinogradov EV, Kaca W, Shashkov AS, Knirel YA "Isolation using triflic acid solvolysis and identification of Ne-[(R)-1-carboxyethyl]-Na-(D-galacturonoyl)-L-lysine as a component of the O-specific polysaccharide of Proteus mirabilis O13" -
Carbohydrate Research328(3) (2000) 441-444
An amino acid was released from the O-specific polysaccharide of Proteus mirabilis O13 by acid hydrolysis and identified as N(ε)-[(R)-1-carboxyethyl]-L-lysine by comparison with the authentic sample. An amide of this amino acid with D-galacturonic acid was isolated from the polysaccharide by solvolysis with anhydrous trifluoromethanesulfonic (triflic) acid and characterised by 1H and 13C NMR spectroscopy. These and published data enabled determination of the full structure of the repeating unit of the polysaccharide.
NCBI PubMed ID:11072853 Publication DOI:10.1016/s0008-6215(00)00106-3 Journal NLM ID:0043535 Publisher: Elsevier Correspondence: knirel@ioc.ac.ru Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Centre of Microbiology and Virology, Polish Academy of Sciences, 93- 232 Lodz, Poland Methods: NMR-2D, NMR, triflic acid solvolysis
Article ID: 1280
Swierzko AS, Cedzynski M, Ziolkowski A, Senchenkova SN, Perepelov AV, Knirel YA, Kaca W "Structure and serological characterization of an Ne-[(R)-1-carboxyethyl)-L-lysine-containing O-chain of the lipopolysaccharide of Proteus mirabilis O13" -
Archivum Immunologiae et Therapiae Experimentalis49(2) (2001) 163-169
In this paper we present the structure and describe serological properties of the O-specific polysaccharide of Proteus mirabilis O13 lipopolysaccharide, which contains a unique component: an amide of D-galacturonic acid (D-GalA) with an unusual amino acid, Nε-[(R)-1-carboxyethyl]-L-lysine (alaninolysine, AlaLys). Selective chemical degradations of either GalA or AlaLys resulted in the loss of the serological reactivity of the polysaccharide with anti-O serum against P. mirabilis O13. Neither synthetic stereoisomers of AlaLys nor the isolated amide of GalA with AlaLys inhibited the reaction of the O-antiserum with the homologous lipopolysaccharide. The O-antiserum did not cross-react with the lipopolysaccharide of Providencia alcalifaciens O23 containing an amide of D-glucuronic acid with AlaLys. These data showed that both uronic acid and amino acid components of the amide play an important role in manifesting the P. mirabilis O13-specificity, but the full specific epitope also includes another O-specific polysaccharide component(s). A cross-reactivity of anti-O13 serum with some other P. mirabilis strains was observed and attributed to a common heat-stable antigen(s) different from the lipopolysaccharide.
NCBI PubMed ID:11348021 Journal NLM ID:0114365 Publisher: Basel, Boston: Birkhaüser Correspondence: mxedzyns@wirus.cmiwpan.lodz.pl Institutions: Centre of Microbiology and Virology, Polish Academy of Sciences, Lodowa 106, 93-232, Lodf, Poland, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia Methods: 13C NMR, 1H NMR, serological methods, triflic acid solvolysis
Article ID: 1467
Knirel YA, Kaca W, Rozalski A, Sidorczyk Z "Structure of the O-antigenic polysaccharides of Proteus bacteria" -
Polish Journal of Chemistry73 (1999) 895-907
Data on the composition and structure of the O-specific polysaccharides (O-antigens) of the lipopolysaccharides of the genus Proteus are summarized and discussed as the molecular basis for serotyping of these medically important bacteria.
Journal NLM ID:7901356 WWW link:http://www.ichf.edu.pl/pjch/pj-1999/pj0699.htm#0895 Publisher: Państwowe Wydawnictwo Naukowe Correspondence: knirel@ioc.ac.ru Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences,Leninsky Prospekt 47, Moscow, Russia, Institute of Microbiology and Immunology, University of Łódź, Banacha 12/16, 90-237 Łódź, Poland, Center of Microbiology and Virology, Polish Academy of Sciences, Lodowa 106, 93-232 Łódź, Poland
Article ID: 3435
Arabski M, Graboski S, Konieczna I, Kaca W, Kondakova AN, Perepelov AV, Senchenkova SN, Shashkov AS, Knirel YA "Serotyping of clinical isolates belonging to Proteus mirabilis serogroup O36 and structural elucidation of the O36-antigen polysaccharide" -
FEMS Immunology and Medical Microbiology53(3) (2008) 395-403
The O-specific polysaccharide (OPS) isolated from the lipopolysaccharide of Proteus mirabilis O36 was found to have a pentasaccharide repeating unit of the following structure: →2)-β-D-Ribf-(1→4)-β-D-Galp-(1→4)-α-D-GlcpNAc6Ac-(1→4)-β-D-Galp-(1→3)-α-D-GlcpNAc-(1→. The structure is unique among Proteus OPS, which is in agreement with the classification of this strain into a separate Proteus O-serogroup. Remarkably, the P. mirabilis O36-polysaccharide has the same structure as the OPS of Escherichia coli O153, except that the latter is devoid of O-acetyl groups. The cross-reaction of anti-O36 antibodies with the O-part of E. coli O153 lipopolysaccharide is observed. In the present study, two steps of serotyping Proteus strains are proposed: screening of dry mass with enzyme-linked immunosorbent assay and immunoblot with the crude lipopolysaccharides. This method allowed serotyping of 99 P. mirabilis strains infecting the human urinary tract. Three strains were classified into serogroup O36. The migration pattern of these lipopolysaccharides fraction with long O-specific PSs was similar to the standard laboratory P. mirabilis O36 (Prk 62/57) lipopolysaccharide. The relatively low number of clinical strains belonging to serogroup O36 did not correspond to the presence of anti-P. mirabilis O36 antibodies in the blood donors' sera. Twenty-five percent of tested sera contained a statistically significant elevated level of antibodies reacting with thermostable surface antigens of P. mirabilis O36. The presence and amount of antibodies correlated with Thr399Ile TLR4 polymorphism types (P=0.044).
NCBI PubMed ID:18625011 Publication DOI:10.1111/j.1574-695X.2008.00440.x Journal NLM ID:9315554 Publisher: Elsevier Correspondence: arabski@pu.kielce.pl Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Department of Microbiology, Institute of Biology, Świętokrzyska Academy, ul. Świę tokrzyska 15,25-406, Kielce, Poland, Department of General Microbiology, Institute of Microbiology and Immunology, University of Łódź, Banacha, Łódź, Poland Methods: 13C NMR, 1H NMR, NMR-2D, chemical analysis, GLC, serological methods, genetic methods
Article ID: 3724
Kwinkowski M, Grabowski S, Konieczna I, Nazarenko EL, Kaca W "The cross-reactivity of Shewanella fidelis lipopolysaccharide with anti-Proteus antibodies" -
Polish Journal of Microbiology58(3) (2009) 275-278
The serological cross-reactivity between lipopolysaccharides (LPS) of S. fidelis KMM3582(T) and rabbit anti-O P. mirabilis antibodies was tested. Using ELISA and Western blot cross-reactivity between S. fidelis LPS and antisera against P. mirabilis O14, O3 LPSs was found. The observed cross-reaction may suggest that anti-P. mirabilis S1959 (O3) antibodies may bind to the internal part of S. fidelis O-polysaccharides. A weak interaction between S. fidelis LPS and antiserum against P. mirabilis O13 in Western blot suggests that the absolute configuration of non-sugar 'AlaLys' component (N(ε)-[(S)-l-carboxyethyl]-N(α)-(D-galacturonoyl)-L-lysine) may influence the affinity of antibodies for S. fidelis LPS.
NCBI PubMed ID:19899622 Journal NLM ID:101229003 Publisher: Polskie Towarzystwo Mikrobiologow Correspondence: marek.kwinkowski@ujk.edu.pl Institutions: Department of Microbiology, Institute of Biology, Jan Kochanowski University, Kielce, Poland Methods: ELISA, serological methods
Article ID: 3869
Kabanov DS, Prokhorenko IR "Structural analysis of lipopolysaccharides from Gram-negative bacteria" -
Biochemistry (Moscow)75(4) (2010) 383-404
This review covers data on composition and structure of lipid A, core, and O-polysaccharide of the known lipopolysaccharides from Gram-negative bacteria. The relationship between the structure and biological activity of lipid A is discussed. The data on roles of core and O-polysaccharide in biological activities of lipopolysaccharides are presented. The structural homology of some oligosaccharide sequences of lipopolysaccharides to gangliosides of human cell membranes is considered.
core, Lipooligosaccharide, O-antigen, lipid A, gangliosides, cytokines, lipopolysaccharide (endotoxin)
NCBI PubMed ID:20618127 Publication DOI:10.1134/S0006297910040012 Journal NLM ID:0376536 Publisher: Nauka/Interperiodica Correspondence: kabanovd1@rambler.ru Institutions: Institute of Basic Biological Problems, Russian Academy of Sciences, Pushchino, Russia
Article ID: 4043
Kaca W, Glenska J, Lechowicz L, Grabowski S, Brauner A, Kwinkowski M "Serotyping of Proteus mirabilis clinical strains based on lipopolysaccharide O-polysaccharide and core oligosaccharide structures" -
Biochemistry (Moscow)76(7) (2011) 851-861
The aim of this work was to serotype Proteus mirabilis urinary tract infection (UTI) strains based on chemically defined O-antigens with the use of two clinical collections from Sweden and Poland consisting of 99 and 24 UTI strains, respectively. A simple two-step serotyping scheme was proposed using enzyme immunoassay with heat-stable surface antigens of Proteus cells and immunoblotting with isolated lipopolysaccharides (LPSs). Using polyclonal anti-P. mirabilis rabbit antisera, 50 Swedish and 8 Polish strains were classified into serogroups O10, O38, O36, O30, O17, O23, O9, O40, O49, O27, O5, O13, O24, O14, and O33. From the Swedish strains, 10 belonged to serogroup O10 and five to each of serogroups O38, O36, and O9. Therefore, none of the O-serogroups was predominant. The majority of the serotyped clinical strains possess acidic O-antigens containing uronic acids and various acidic non-carbohydrate substituents. In immunoblotting, antisera cross-reacted with both O-antigen and core of LPSs. The core region of 19 LPSs bound a single serum, and that of 12 LPSs bound more than two sera. Following bioinformatic analysis of the available sequences, a molecular approach to the prediction of Proteus core oligosaccharide structures was proposed. The identification of the core type of P. mirabilis R110, derived from a serogroup O3 wild strain, using restriction fragments length polymorphism analysis of galacturonic acid transferase is shown as an example. In summary, the most frequent O-serogroups among P. mirabilis UTI stains were identified. The diversity of serological reactions of LPSs is useful for serotyping of P. mirabilis clinical isolates. A possible role of the acidic components of O-antigens in UTI is discussed.
NCBI PubMed ID:21999547 Publication DOI:10.1134/S0006297911070169 Journal NLM ID:0376536 Publisher: Nauka/Interperiodica Correspondence: wieslaw.kaca@ujk.edu.pl Institutions: Department of Microbiology, Institute of Biology, Jan Kochanowski University, Kielce, Poland Methods: PCR, SDS-PAGE, EIA, serological methods, immunoblotting, bioinformatic analysis
Article ID: 4049
Knirel YA, Perepelov AV, Kondakova AN, Senchenkova SN, Sidorczyk Z, Rozalski A, Kaca W "Structure and serology of O-antigens as the basis for classification of Proteus strains" -
Innate Immunity17(1) (2011) 70-96
This review is devoted to structural and serological characteristics of the O-antigens (O-polysaccharides) of the lipopolysaccharides of various Proteus species, which provide the basis for classifying Proteus strains to O-serogroups. The antigenic relationships of Proteus strains within and beyond the genus as well as their O-antigen-related bioactivities are also discussed.
NCBI PubMed ID:20305038 Publication DOI:10.1177/1753425909360668 Journal NLM ID:101469670 Publisher: Sage Publications Correspondence: yknirel@gmail.com Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Institute of Microbiology, Biotechnology and Immunology, University of Lodz, Lodz, Poland, Department of Microbiology, Jan Kochanowski University, Kielce, Poland
Article ID: 4822
Palusiak A, Siwinska M, Zabłotni A "Proteus mirabilis RMS 203 as a new representative of the O13 Proteus serogroup" -
Acta Biochimica Polonica62(4) (2015) 691-695
The unique feature of some Proteus O-polysaccharides is occurrence of an amide of galacturonic acid with Nε-[(S/R)-1-Carboxyethyl]-l-lysine, GalA6(2S,8S/R-AlaLys). The results of the serological studies presented here, with reference to known O-antigens structures suggest that GalA6(2S,8S/R-AlaLys) or 2S,8R-AlaLys contribute to cross-reactions of O13 Proteus antisera, and Proteeae LPSs. It was also revealed that the Proteus mirabilis RMS 203 strain can be classified into the O13 serogroup, represented so far by two strains: Proteus mirabilis 26/57 and Proteus vulgaris 8344. The O13 LPS is a serologically important antigen with a fragment common to LPSs of different species in the Proteeae tribe.
NCBI PubMed ID:26645323 Publication DOI:10.18388/abp.2015_1108 Journal NLM ID:14520300R Publisher: Panstwowe Wydawnictwo Naukowe Correspondence: agatapal@biol.uni.lodz.pl Institutions: Department of General Microbiology, Institute of Microbiology, Biotechnology and Immunology, University of Łódź, Łódź, Poland Methods: serological methods
Article ID: 5423
Dobrochaeva KL, Khasbiulina NR, Shilova NV, Obukhova PS, Knirel YA, Nokel AY, Bovin NV "Human antibodies eluted from ligand-free Sepharose capable of binding bacterial polysaccharides and sulfated glycans" -
Molecular Immunology106 (2019) 63-68
Sepharose matrix without immobilized ligands binds antibodies from human blood serum or immunoglobulin preparations. The eluted antibodies bind bacterial polysaccharides having no structural similarity to agarose (Sepharose is a cross-linked polysaccharide agarose) with a high affinity. It is concluded that the identified antibodies are capable of recognizing spatial rather than linear epitopes of bacterial polysaccharides. This side activity of Sepharose matrix should be taken into account in isolating target antibodies and other proteins from human blood.
NCBI PubMed ID:30583222 Publication DOI:10.1016/j.molimm.2018.12.011 Journal NLM ID:7905289 Publisher: Elsevier Correspondence: N.V. Bovin Institutions: Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, 16/10 ul. Miklukho-Maklaya, Moscow, Russian Federation, Semiotik LLC, Moscow, Russian Federation, N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky pr., Moscow, Russian Federation, School of Engineering, Computer & Mathematical Sciences, Auckland University of Technology, Auckland 1010, New Zealand Methods: serological methods, UV, affinity chromatography, antibody binding, glycan array analysis, microarray binding assays, serum analysis, isolation of antibodies
Article ID: 5760
Dobrochaeva K, Khasbiulina N, Shilova N, Antipova N, Obukhova P, Galanina O, Blixt O, Kunz H, Filatov A, Knirel Y, Le Pendu J, Khaidukov S, Bovin N "Specificity of human natural antibodies referred to as anti-Tn" -
Molecular Immunology120 (2020) 74-82
To understand the role of human natural IgM known as antibodies against the carbohydrate epitope Tn, the antibodies were isolated using GalNAcα-Sepharose affinity chromatography, and their specificity was profiled using microarrays (a glycan array printed with oligosaccharides and bacterial polysaccharides, as well as a glycopeptide array), flow cytometry, and inhibition ELISA. The antibodies bound a restricted number of GalNAcα-terminated oligosaccharides better than the parent monosaccharide, e.g., 6-O-Su-GalNAcα and GalNAcα1-3Galβ1-3(4)GlcNAcβ. The binding with several bacterial polysaccharides that have no structural resemblance to the affinity ligand GalNAcα was quite unexpected. Given that GalNAcα is considered the key fragment of the Tn antigen, it is surprising that these antibodies bind weakly GalNAcα-OSer and do not bind a wide variety of GalNAcα-OSer/Thr-containing mucin glycopeptides. At the same time, we have observed specific binding to cells having Tn-positive glycoproteins containing similar glycopeptide motifs in a conformationally rigid macromolecule. Thus, specific recognition of the Tn antigen apparently requires that the naturally occurring "anti-Tn" IgM recognize a complex epitope comprising the GalNAcα as an essential component and a fairly long amino acid sequence where the amino acids adjacent to GalNAcα do not contact the antibody paratope; i.e., the antibodies recognize a spatial epitope or a molecular pattern rather than a classical continuous sequence. In addition, we have not found any increase in the binding of natural antibodies when GalNAcα residues were clustered. These results may help in further development of anticancer vaccines based on synthetic Tn constructs.
NCBI PubMed ID:32087569 Publication DOI:10.1016/j.molimm.2020.02.005 Journal NLM ID:7905289 Publisher: Elsevier Correspondence: professorbovin@yandex.ru Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, 16/10 Miklukho-Maklaya, Moscow, Russian Federation, Semiotik LLC, 16/10 Miklukho-Maklaya, Moscow, Russian Federation, National Medical Research Center for Obstetrics, Gynecology and Perinatology Named after Academician V.I. Kulakov of the Ministry of Healthcare of Russian Federation, Moscow, Russian Federation, National Research University Higher School of Economics, Moscow, Russian Federation, Department of Chemistry, Chemical Biology, University of Copenhagen, Thorvaldsensvej 40, 1871 Frederiksberg C, Denmark, Institut Fur Organische Chemie, Johannes Gutenberg-Universitat Mainz, Duesbergweg 10-14, D-55128, Mainz, Germany, Institute of Immunology, Federal Medical-Biological Agency of Russia, Moscow, Russian Federation, University of Nantes, Inserm, U892 IRT UN, 8 Quai MonCousu, BP70721 Nantes, FR 44007, France Methods: ELISA, affinity chromatography, flow cytometry analysis, printed glycan array (PGA) analysis, FACS assay
The structure is contained in the following publication(s):
Article ID: 877
Kocharova NA, Zatonsky GV, Torzewska A, Macieja Z, Bystrova OV, Shashkov AS, Knirel YA, Rozalski A "Structure of the O-specific polysaccharide of Providencia rustigianii O14 containing Na-[(S)-1-carboxyethyl]-Ne-(D-galacturonoyl)-L-lysine" -
Carbohydrate Research338(9) (2003) 1009-1016
The O-specific polysaccharide of Providencia rustigianii O14 was obtained by mild acid degradation of the LPS and studied by chemical methods and NMR spectroscopy, including 2D 1H,(1)H COSY, TOCSY, NOESY, and 1H,(13)C HSQC experiments. The polysaccharide was found to contain N(ε)-[(S)-1-carboxyethyl]-N(α)-(D-galacturonoyl)-L-lysine ('alaninolysine', 2S,8S-AlaLys). The amino acid component was isolated by acid hydrolysis and identified by 13C NMR spectroscopy and specific optical rotation, using synthetic diastereomers for comparison. The following structure of the trisaccharide repeating unit of the polysaccharide was established: . Anti-P. rustigianii O14 serum was found to cross-react with O-specific polysaccharides of Providencia and Proteus strains that contains amides of uronic acid with N(ε)-[(R)-1-carboxyethyl]-L-lysine and L-lysine.
structure, O-specific polysaccharide, Providencia alcalifaciens, Alaninolysine, bacterial polysaccharide structures, Nα-(D-galacturonoyl)-Nε-[(S)-1-carboxyethyl)-L-lysine, Providencia rustigianii, Providencia rustigianii; published polymerization frame was shifted for conformity with other records.
NCBI PubMed ID:12681927 Publication DOI:10.1016/S0008-6215(03)00019-3 Journal NLM ID:0043535 Publisher: Elsevier Correspondence: rozala@biol.uni.lodz.pl Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospekt 47, 119991 Moscow, GSP-1, Russia, Department of Immunobiology of Bacteria, Institute of Microbiology and Immunology, University of Lodz, Banacha 12/16, 90-237 Lodz, Poland Methods: methylation, NMR, acid hydrolysis
The structure is contained in the following publication(s):
Article ID: 1091
Perepelov AV, Senchenkova SN, Cedzynski M, Ziolkowski A, Vinogradov EV, Kaca W, Shashkov AS, Knirel YA "Isolation using triflic acid solvolysis and identification of Ne-[(R)-1-carboxyethyl]-Na-(D-galacturonoyl)-L-lysine as a component of the O-specific polysaccharide of Proteus mirabilis O13" -
Carbohydrate Research328(3) (2000) 441-444
An amino acid was released from the O-specific polysaccharide of Proteus mirabilis O13 by acid hydrolysis and identified as N(ε)-[(R)-1-carboxyethyl]-L-lysine by comparison with the authentic sample. An amide of this amino acid with D-galacturonic acid was isolated from the polysaccharide by solvolysis with anhydrous trifluoromethanesulfonic (triflic) acid and characterised by 1H and 13C NMR spectroscopy. These and published data enabled determination of the full structure of the repeating unit of the polysaccharide.
NCBI PubMed ID:11072853 Publication DOI:10.1016/s0008-6215(00)00106-3 Journal NLM ID:0043535 Publisher: Elsevier Correspondence: knirel@ioc.ac.ru Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Centre of Microbiology and Virology, Polish Academy of Sciences, 93- 232 Lodz, Poland Methods: NMR-2D, NMR, triflic acid solvolysis
The structure is contained in the following publication(s):
Article ID: 1280
Swierzko AS, Cedzynski M, Ziolkowski A, Senchenkova SN, Perepelov AV, Knirel YA, Kaca W "Structure and serological characterization of an Ne-[(R)-1-carboxyethyl)-L-lysine-containing O-chain of the lipopolysaccharide of Proteus mirabilis O13" -
Archivum Immunologiae et Therapiae Experimentalis49(2) (2001) 163-169
In this paper we present the structure and describe serological properties of the O-specific polysaccharide of Proteus mirabilis O13 lipopolysaccharide, which contains a unique component: an amide of D-galacturonic acid (D-GalA) with an unusual amino acid, Nε-[(R)-1-carboxyethyl]-L-lysine (alaninolysine, AlaLys). Selective chemical degradations of either GalA or AlaLys resulted in the loss of the serological reactivity of the polysaccharide with anti-O serum against P. mirabilis O13. Neither synthetic stereoisomers of AlaLys nor the isolated amide of GalA with AlaLys inhibited the reaction of the O-antiserum with the homologous lipopolysaccharide. The O-antiserum did not cross-react with the lipopolysaccharide of Providencia alcalifaciens O23 containing an amide of D-glucuronic acid with AlaLys. These data showed that both uronic acid and amino acid components of the amide play an important role in manifesting the P. mirabilis O13-specificity, but the full specific epitope also includes another O-specific polysaccharide component(s). A cross-reactivity of anti-O13 serum with some other P. mirabilis strains was observed and attributed to a common heat-stable antigen(s) different from the lipopolysaccharide.
NCBI PubMed ID:11348021 Journal NLM ID:0114365 Publisher: Basel, Boston: Birkhaüser Correspondence: mxedzyns@wirus.cmiwpan.lodz.pl Institutions: Centre of Microbiology and Virology, Polish Academy of Sciences, Lodowa 106, 93-232, Lodf, Poland, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia Methods: 13C NMR, 1H NMR, serological methods, triflic acid solvolysis
The structure is contained in the following publication(s):
Article ID: 4049
Knirel YA, Perepelov AV, Kondakova AN, Senchenkova SN, Sidorczyk Z, Rozalski A, Kaca W "Structure and serology of O-antigens as the basis for classification of Proteus strains" -
Innate Immunity17(1) (2011) 70-96
This review is devoted to structural and serological characteristics of the O-antigens (O-polysaccharides) of the lipopolysaccharides of various Proteus species, which provide the basis for classifying Proteus strains to O-serogroups. The antigenic relationships of Proteus strains within and beyond the genus as well as their O-antigen-related bioactivities are also discussed.
NCBI PubMed ID:20305038 Publication DOI:10.1177/1753425909360668 Journal NLM ID:101469670 Publisher: Sage Publications Correspondence: yknirel@gmail.com Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Institute of Microbiology, Biotechnology and Immunology, University of Lodz, Lodz, Poland, Department of Microbiology, Jan Kochanowski University, Kielce, Poland
Article ID: 5057
Yu X, Torzewska A, Zhang X, Yin Z, Drzewiecka D, Cao H, Liu B, Knirel YA, Rozalski A, Wang L "Genetic diversity of the O antigens of Proteus species and the development of a suspension array for molecular serotyping" -
PLoS One12(8) (2017) e0183267
Proteus species are well-known opportunistic pathogens frequently associated with skin wound and urinary tract infections in humans and animals. O antigen diversity is important for bacteria to adapt to different hosts and environments, and has been used to identify serotypes of Proteus isolates. At present, 80 Proteus O-serotypes have been reported. Although the O antigen structures of most Proteus serotypes have been identified, the genetic features of these O antigens have not been well characterized. The O antigen gene clusters of Proteus species are located between the cpxA and secB genes. In this study, we identified 55 O antigen gene clusters of different Proteus serotypes. All clusters contain both the wzx and wzy genes and exhibit a high degree of heterogeneity. Potential functions of O antigen-related genes were proposed based on their similarity to genes in available databases. The O antigen gene clusters and structures were compared, and a number of glycosyltransferases were assigned to glycosidic linkages. In addition, an O serotype-specific suspension array was developed for detecting 31 Proteus serotypes frequently isolated from clinical specimens. To our knowledge, this is the first comprehensive report to describe the genetic features of Proteus O antigens and to develop a molecular technique to identify different Proteus serotypes.
NCBI PubMed ID:28817637 Publication DOI:10.1371/journal.pone.0183267 Journal NLM ID:101285081 Publisher: San Francisco, CA: Public Library of Science Correspondence: Lei Wang Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, TEDA Institute of Biological Sciences and Biotechnology, Nankai University, Tianjin, P. R. China, Tianjin Research Center for Functional Genomics and Biochips, TEDA College, Nankai University, Tianjin, P. R. China, Tianjin Key Laboratory of Microbial Functional Genomics, TEDA College, Nankai University, Tianjin, P. R. China, Key Laboratory of Molecular Microbiology and Technology of the Ministry of Education, TEDA College, Nankai University, Tianjin, P. R. China, Department of Immunobiology of Bacteria, Department of General Microbiology Institute of Microbiology, Biotechnology and Immunology, Faculty of Biology and Environmental Protection, University of Lodz, Lodz, Poland Methods: PCR, DNA sequencing, genetic methods, function analysis of gene clusters, serotyping
Article ID: 6050
Drzewiecka D, Palusiak A, Siwinska M, Zablotni A "The prevailing O serogroups among the serologically differentiated clinical Proteus spp. strains in central Poland" -
Scientific Reports11(1) (2021) 18982
In the years 2006-2011, 617 Proteus spp. strains isolated mostly from urine and wounds or other clinical sources were collected in Lodz, Poland, to determine the offensive O serotypes frequently occurring among patients. P. mirabilis exhibited the most intensive swarming growth and was dominating species (86.9%), followed by P. genomospecies, P. vulgaris, and P. penneri. Ninety four per cent strains were recognized as S (smooth) forms. Serological studies (involving ELISA-enzyme-linked immunosorbent assay and Western blotting using native and adsorbed rabbit antisera) enabled classification of 80% S isolates into respective Proteus O serogroups among the 83 ones, described so far. The remaining strains seemed to be serologically unique. Despite the observed big serological variety of Proteus spp. isolates, we found the O78 serogroup recently described in Poland as dominating and identified other widespread serotypes: O3, O6, O10, O11, O27, O28, and O30 reported earlier as predominating also in other countries; O77 and O79 detected lately in Poland; O16, O18, O20, and O50. No unique structural feature of the prevalent O serotypes has been indicated. However, the prevalence of some O serogroups indicates that particular serotypes may be in some ways beneficial to the strains producing these kinds of O antigen.
clinical, strain, O antigen, Proteus, serogroup, Serotypes, ELISA, O serotype
NCBI PubMed ID:34556711 Publication DOI:10.1038/s41598-021-98228-w Journal NLM ID:101563288 Publisher: London: Nature Publishing Group Correspondence: dominika.drzewiecka@biol.uni.lodz.pl Institutions: Department of Biology of Bacteria, Faculty of Biology and Environmental Protection, University of Łódź, Banacha 12/16, 90-237, Łódź, Poland Methods: ELISA, Western blotting, serological methods, serotyping analysis
The structure is contained in the following publication(s):
Article ID: 4051
Kocharova NA, Ovchinnikova OG, Bialczak-Kokot M, Shashkov AS, Knirel YA, Rozalski A "Structure of the O-polysaccharide of Providencia alcalifaciens O25 containing an amide of D-galacturonic acid with Ne-[(R)-1-carboxyethyl]-L-lysine" -
Biochemistry (Moscow)76(6) (2011) 707-712
An acidic O-polysaccharide was isolated by mild acid degradation of the lipopolysaccharide of Providencia alcalifaciens O25 followed by gel-permeation and anion-exchange chromatography. The O-polysaccharide was studied by sugar and methylation analyses along with (1)H and (13)C NMR spectroscopy, including two-dimensional correlation (1)H,(13)C HMBC, and (1)H,(1)H ROESY experiments both in D(2)O and, to detect correlations for NH protons, in a 9 : 1 H(2)O/D(2)O mixture. An amino acid was isolated from the polysaccharide by acid hydrolysis and identified as N(?)-[(R)-1-carboxyethyl]-L-lysine ('alaninolysine', 2S,8R-alaLys) by determination of the specific optical rotation and (13)C NMR spectroscopy, using the authentic synthetic diastereomers 2S,8R-alaLys and 2S,8S-alaLys for comparison. The structure of the branched tetrasaccharide repeating unit of the O-polysaccharide was established.
NCBI PubMed ID:21639852 Journal NLM ID:0376536 Publisher: Nauka/Interperiodica Correspondence: olga.ovchinnikova@gmail.com Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia Methods: 13C NMR, 1H NMR, methylation, GLC-MS, NMR-2D, sugar analysis
Article ID: 4329
Knirel YA "Structure of O-antigens" -
Book: Bacterial lipopolysaccharides: Structure, chemical synthesis, biogenesis and interaction with host cells (2011) Chapter 3, 41-115
The lipopolysaccharide (LPS) is the major constituent of the outer leaflet of the outer membrane of Gram-negative bacteria. Its lipid A moiety is embedded in the membrane and serves as an anchor for the rest of the LPS molecule. The outermost repetitive glycan region of the LPS is linked to the lipid A through a core oligosaccharide (OS), and is designated as the O-specific polysaccharide (O-polysaccharide, OPS) or O-antigen. The O-antigen is the most variable portion of the LPS and provides serological specificity, which is used for bacterial serotyping. The OPS also provides protection to the microorganisms from host defenses such as complement mediated killing and phagocytosis, and is involved in interactions of bacteria with plants and bacteriophages. Studies of the OPSs ranging from the elucidation of their chemical structures and conformations to their biological and physico-chemical properties help improving classification schemes of Gram-negative bacteria. Furthermore, these studies contributed to a better understanding of the mechanisms of pathogenesis of infectious diseases, as well as provided information to develop novel vaccines and diagnostic reagents.
Lipopolysaccharide, synthesis, lipopolysaccharides, structure, Bacterial, host, O-antigen, O antigen, cell, O antigens, O-antigens, chemical, interaction, cells, PDF, chemical synthesis, biogenesis
Publication DOI:10.1007/978-3-7091-0733-1_3 Publisher: Springer Correspondence: knirel@ioc.ac.ru Editors: Knirel YA, Valvano MA Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
Article ID: 4589
Ovchinnikova OG, Rozalski A, Liu B, Knirel YA "O-Antigens of bacteria of the genus Providencia: structure, serology, genetics, and biosynthesis" -
Biochemistry (Moscow)78(7) (2013) 798-817
The genus Providencia consists of eight species of opportunistic pathogenic enterobacteria that can cause enteric diseases and urinary tract infections. The existing combined serological classification scheme of three species, P. alcalifaciens, P. stuartii, and P. rustigianii, is based on the specificity of O-antigens (O-polysaccharides) and comprises 63 O-serogroups. Differences between serogroups are related to polymorphism at a specific genome locus, the O-antigen gene cluster, responsible for O-antigen biosynthesis. This review presents data on structures of 36 O-antigens of Providencia, many of which contain unusual monosaccharides and non-carbohydrate components. The structural data correlate with the immunospecificity of the O-antigens and enable substantiation on a molecular level of serological relationships within the genus Providencia and between strains of Providencia and bacteria of the genera Proteus, Escherichia, and Salmonella. Peculiar features of the O-antigen gene cluster organization in 10 Providencia serogroups and biosynthetic pathways of nucleotide precursors of specific monosaccharide components of the O-antigens also are discussed.
NCBI PubMed ID:24010842 Publication DOI:10.1134/S0006297913070110 Journal NLM ID:0376536 Publisher: Nauka/Interperiodica Correspondence: olga.ovchinnikova@gmail.com Institutions: ND Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Department of Immunobiology of Bacteria, Institute of Microbiology, Biotechnology and Immunology, University of Lodz, PL 90-237 Lodz, Poland, TEDA School of Biological Sciences and Biotechnology, Nankai University, 23 Hongda Street, TEDA, 300457 Tianjin, P. R. China
The structure is contained in the following publication(s):
Article ID: 5057
Yu X, Torzewska A, Zhang X, Yin Z, Drzewiecka D, Cao H, Liu B, Knirel YA, Rozalski A, Wang L "Genetic diversity of the O antigens of Proteus species and the development of a suspension array for molecular serotyping" -
PLoS One12(8) (2017) e0183267
Proteus species are well-known opportunistic pathogens frequently associated with skin wound and urinary tract infections in humans and animals. O antigen diversity is important for bacteria to adapt to different hosts and environments, and has been used to identify serotypes of Proteus isolates. At present, 80 Proteus O-serotypes have been reported. Although the O antigen structures of most Proteus serotypes have been identified, the genetic features of these O antigens have not been well characterized. The O antigen gene clusters of Proteus species are located between the cpxA and secB genes. In this study, we identified 55 O antigen gene clusters of different Proteus serotypes. All clusters contain both the wzx and wzy genes and exhibit a high degree of heterogeneity. Potential functions of O antigen-related genes were proposed based on their similarity to genes in available databases. The O antigen gene clusters and structures were compared, and a number of glycosyltransferases were assigned to glycosidic linkages. In addition, an O serotype-specific suspension array was developed for detecting 31 Proteus serotypes frequently isolated from clinical specimens. To our knowledge, this is the first comprehensive report to describe the genetic features of Proteus O antigens and to develop a molecular technique to identify different Proteus serotypes.
NCBI PubMed ID:28817637 Publication DOI:10.1371/journal.pone.0183267 Journal NLM ID:101285081 Publisher: San Francisco, CA: Public Library of Science Correspondence: Lei Wang Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, TEDA Institute of Biological Sciences and Biotechnology, Nankai University, Tianjin, P. R. China, Tianjin Research Center for Functional Genomics and Biochips, TEDA College, Nankai University, Tianjin, P. R. China, Tianjin Key Laboratory of Microbial Functional Genomics, TEDA College, Nankai University, Tianjin, P. R. China, Key Laboratory of Molecular Microbiology and Technology of the Ministry of Education, TEDA College, Nankai University, Tianjin, P. R. China, Department of Immunobiology of Bacteria, Department of General Microbiology Institute of Microbiology, Biotechnology and Immunology, Faculty of Biology and Environmental Protection, University of Lodz, Lodz, Poland Methods: PCR, DNA sequencing, genetic methods, function analysis of gene clusters, serotyping
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