Show legend Show as text

Structure type: oligomer
Aglycon: p-trifluoroacetamidophenyl
Contained glycoepitopes: IEDB_136045,IEDB_136105,IEDB_1394181,IEDB_142489,IEDB_144562,IEDB_152214,IEDB_174333,IEDB_225177,IEDB_885823,SB_86

• Article ID: 622
  Bajza I, Kover KE, Lipták A "Synthesis of p-trifluoroacetamidophenyl (4,6-dideoxy-4-formamido-3-C-methyl-2-O-methyl-a-L-mannopyranosyl)-(1->3)-(2-O-methyl-a-L-rhamnopyranosyl)-(1->3)-(2-O-methyl-a-L-fucopyranosyl)-(1->3)-(a-L-rhamnopyranosyl)-(1->2)-6-deoxy-a-L-talopyranoside: a spacer-armed pentasaccharide glycopeptidolipid antigen of Mycobacterium avium serovar 14" - Carbohydrate Research 308 (1998) 247-258
  

  Syntheses of p-trifluoroacetamidophenyl glycosides of the haptenic pentasaccharide and the non-reducing disaccharide unit of the title pentasaccharide are reported. The synthesis of the terminal N-formylkansosamine unit started from methyl 6-deoxy-2,3-O-isopropylidene-a-L-lyxo-hexopyran-4-uloside which, after C-3 methylation, was transformed into a glycosyl donor [3-O-benzyl-4-N-benzylformamido-4,6-dideoxy-3-C-methyl-2-O-methyl-a,b-L-mannopyranosyl trichloroacetimidate (20), and used for the synthesis of p-trifluoroacetamidophenyl (4-formamido-4,6-dideoxy-3-C-methyl-2-O-methyl-a-L-mannopyranosyl)-(l→3)-6-deoxy-2-O-methyl-a-D-mannopyranoside (29). Ethyl (3-O-benzyl-4-N-benzylformamido-4,6-dideoxy-3-C-methyl-2-O-methyl-a-L-mannopyranosyl)-(l→3)-4-O-benzyl-6-deoxy-2-O-methyl-l-thio-a-D-mannopyranoside (31), prepared by glycosylation of ethyl 4-O-benzyl-6-deoxy-2-O-methyl-l-thio-a-D-mannopyranoside with 20, served as glycosyl donor in a 2+3 block synthesis of the title pentasaccharide.

  synthesis, antigen, polysaccharide, oligosaccharide synthesis, Mycobacterium, block synthesis, glycopeptidolipid, hapten, Mycobacteria, Mycobacterium avium, pentasaccharide, Branched-chain sugar, spacer

  NCBI PubMed ID: 9711823
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Institutions: Research Group for Carbohydrates of the Hungarian Academy of Sciences, Debrecen, P.O.B 55, H-4010 Hungary, Institute of Organic Chemistry, L. Kossuth University, Debrecen, P.O.B. 20, H-4010 Hungary, Institute of Biochemistry, L. Kossuth University, Debrecen, P.O.B 55, H-4010 Hungary
  Methods: NMR
  
   
  
  Mycobacterium avium 14
  CSDB ID 77 (all data & tools)

Show legend Show as text

Structure type: oligomer
Aglycon: N-acylpeptide LIP(1-2)xDPhe(1-2)xDaThr(1-2)xDAla?(1-2)Subst // Subst = alaninol = SMILES N{2}[C@@H](C){1}CO
Trivial name: oligosaccharide hapten
Compound class: glycopeptidolipid (GPL)
Contained glycoepitopes: IEDB_115136,IEDB_136098,IEDB_136105,IEDB_140630,IEDB_225177,IEDB_423153,IEDB_885823

• Article ID: 1451
  Chatterjee D, Khoo KH "The surface glycopeptidolipids of mycobacteria: structures and biological properties" - Cellular and Molecular Life Sciences 58(14) (2001) 2018-2042
  

  One of the most important opportunistic pathogens associated with acquired immunodeficiency syndrome (AIDS) is the M. avium complex. M. avium infections are found in up to 70% of individuals in advanced stages of AIDS. It is apparent that M. avium can replicate in host macrophages and persist for long periods. This group of mycobacteria are distinguished by the presence of unique, highly antigenic, surface- located lipids known as the glycopeptidolipids (GPLs). The GPLs are the chemical basis of the 31 distinct serovars of the M. avium complex, and have also been identified in some other species. The M. avium lipids are immunosuppressive and can induce a variety of cytokines that affect general host responses. Despite extensive chemical characterization of the structures of these GPLs, much work is needed to elucidate the molecular mechanism involved in this complex glycosylation pathway and its genetic basis. The challenges for the future lie in explaining the roles of these copious products in the intracellular life and infectivity of mycobacteria. The intention of our review is to offer a concise account of the structures of the M. avium lipids, their putative roles in the host responses, bacterial physiology and pathogenesis, particularly in immunocompromised patients such as those infected with human immunodeficiency virus (HIV). Advances in chemical synthesis of the various haptenic oligosaccharides are also given to demonstrate how these have helped to define the immunogenic determinants. We believe that future research should involve the creation of conditional mutants defective in these lipids for both functional and biosynthesis studies which will complement biological assays using chemically defined or modified neoglycoconjugates

  Mycobacteria, neoglycoproteins, glycopeptidolipid (GPL), Mycobacterium avium complex (MAC), haptenic oligosaccharides

  NCBI PubMed ID: 11814054
  Publication DOI: 10.1007/PL00000834
  Journal NLM ID: 9705402
  Publisher: Basel: Springer
  Correspondence: delphi@lamar.colostate.edu
  Institutions: Department of Microbiology, Colorado State University, Fort Collins 80523, USA, Institute of Biological Chemistry, Academia Sinica, Taipei (Taiwan)
  
   
  
  Mycobacterium avium sv. 19
  CSDB ID 31666 (all data & tools)

Show legend Show as text

Structure type: oligomer
Aglycon: peptidolipid
Trivial name: pentasaccharide hapten GPL
Contained glycoepitopes: IEDB_115136,IEDB_136105,IEDB_140630,IEDB_225177,IEDB_423153,IEDB_885823

• Article ID: 3237
  Fekete A, Gyergyoi K, Kover KE, Bajza I, Lipták A "Preparation of the pentasaccharide hapten of the GPL of Mycobacterium avium serovar 19 by achieving the glycosylation of a tertiary hydroxyl group" - Carbohydrate Research 341(10) (2006) 1312-1321
  

  The chemical synthesis of the glycopeptidolipid-type pentasaccharide hapten of Mycobacterium avium serovar 19 with a trifluoroacetamido spacer at the reducing end is described. The spacer-armed pentasaccharide 31, when conjugated to an immunogenic protein, can be applied to the serodiagnosis of mycobacterial infections. The questionable structure of the penultimate monosaccharide unit was clarified as 6-deoxy-3-C-methyl-2,4-di-O-methyl-L-mannopyranose. The occurrence of the 6-deoxy-3-C-methyl-2,4-di-O-methyl-L-talopyranose could be excluded by the presence of the large H-1'-H-2' coupling constant, which proves the 4C1 (L) conformation as the favoured one.

  Oligosaccharides, hapten, Mycobacteria

  NCBI PubMed ID: 16712821
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: liptaka@puma.unideb.hu
  Institutions: Research Group for Carbohydrates of the Hungarian Academy of Sciences, PO Box 94, H-4010 Debrecen, Hungary, Institute of Inorganic and Analytical Chemistry, University of Debrecen, PO Box 21, H-4010 Debrecen, Hungary, Institute of Biochemistry, University of Debrecen, PO Box 55, H-4010 Debrecen, Hungary
  Methods: NMR, chemical synthesis
  
   
  
  Mycobacterium avium sv. 19
  CSDB ID 20058 (all data & tools)

Show legend Show as text

Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_136105,IEDB_1394181,IEDB_145010,IEDB_225177,IEDB_885823

• 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
  
   
  
  Azorhizobium caulinodans
  CSDB ID 27849 (all data & tools)

Show legend Show as text

Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_1394181,IEDB_145010

• Article ID: 4333
  Komaniecka I, Choma A, Zamlynska K, Turska-Szewczuk A, Sowinski P "Structural elucidation of the O-antigen repeating unit of Phyllobacterium trifolii lipopolysaccharide" - Proceedings of 5th Baltic Meeting on Microbial Carbohydrates (5th : 2012 : Suzdal, Russia) (2012) P26
  

  carbohydrates, structural, O-antigen, repeating unit, O antigen, carbohydrate, elucidation, P, Russia

  Correspondence: ikoma@biotop.umcs.lublin.pl
  Institutions: Department of Genetics and Microbiology, Maria Curie-Sklodowska University, Lublin, Poland
  Methods: 13C NMR, 1H NMR, GLC-MS, NMR-2D, composition analysis, NMR-1D
  
   
  
  Phyllobacterium trifolii
  CSDB ID 27215 (all data & tools)
• Article ID: 4871
  Zamlynska K, Komaniecka I, Turska-Szewczuk A, Pac M, Choma A "The O-specific polysaccharides from Phyllobacterium trifolii PETP02(T) LPS contain 3-C-methyl-D-rhamnose" - Carbohydrate Research 409 (2015) 25-29
  

  The O-specific polysaccharides of Phyllobacterium trifolii PETP02(T), a microsymbiont of Trifolium pratense, were obtained by mild acid hydrolysis of the lipopolysaccharide and studied by chemical analyses, mass spectrometry, and (1)H and (13)C NMR spectroscopy, including homonuclear ((1)H,(1)H DQF-COSY, TOCSY, NOESY) and heteronuclear ((1)H,(13)C HSQC, HMQC, HMBC) experiments. It was revealed that α-D-rhamnose and β-3-C-methyl-D-rhamnose (evalose) were the only components of two identified O-polysaccharides. The major O-polysaccharide was found to consist of linear hexasaccharide repeating units, while the other minor one, is composed of disaccharide repeats. The following structures of two O-polysaccharides were established: →2)-β-D-Rhap3CMe-(1→3)-α-D-Rhap-(1→3)-α-D-Rhap-(1→2)-β-D-Rhap3CMe-(1→3)-α-D-Rhap-(1→2)-α-D-Rhap-(1→ and →2)-β-D-Rhap3CMe-(1→3)-α-D-Rhap-(1→.

  Lipopolysaccharide, structure, rhamnose, O-specific polysaccharides, 3-C-methyl-D-rhamnose, evalose, 3-C-Methylrhamnose, Phyllobacterium trifolii

  NCBI PubMed ID: 25917130
  Publication DOI: 10.1016/j.carres.2015.02.013
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: adam.choma@poczta.umcs.lublin.pl
  Institutions: Department of Genetics and Microbiology, Maria Curie-Sklodowska University, Akademicka 19, 20-033 Lublin, Poland
  Methods: 13C NMR, 1H NMR, NMR-2D, GC-MS, SDS-PAGE, mild acid hydrolysis, GC, composition analysis, NMR-1D, GPC
  
   
  
  Phyllobacterium trifolii PETP02(T)
  CSDB ID 11082 (all data & tools)

Show legend Show as text

Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_1394181,IEDB_145010

• Article ID: 4424
  Zdorovenko EL, Valueva OA, Kachala VV, Shashkov AS, Knirel YA, Komaniecka I, Choma A "Structure of the O-polysaccharide of Azorhizobium caulinodans HAMBI 216; identification of 3-C-methyl-D-rhamnose as a component of bacterial polysaccharides" - Carbohydrate Research 358 (2012) 106-109
  

  The O-polysaccharide was obtained from the lipopolysaccharide of the stem-nodulating nitrogen-fixing bacterium Azorhizobium caulinodans HAMBI 216 and studied by sugar and methylation analyses along with (1)H and (13)C NMR spectroscopy. The polysaccharide was found to have a linear pentasaccharide repeating unit containing D-rhamnose and its rarely occurring 2-O-methyl (Rha2OMe) and 3-C-methyl (Rha3CMe) derivatives and having the following structure: →3)-α-D-Rhap2OMe-(1→2)-β-D-Rhap3CMe-(1→3)-α-D-Rhap-(1→2)-β-D-Rhap3CMe-(1→3)-α-D-Rhap-(1→.

  structure, bacterial polysaccharide structure, Azorhizobium caulinodans, lipolysaccharide, 3-C-methyl-D-rhamnose, evalose, 2-O-methyl-D-rhamnose

  NCBI PubMed ID: 22819626
  Publication DOI: 10.1016/j.carres.2012.06.012
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: zdorovenkoe@mail.ru
  Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
  Methods: 13C NMR, 1H NMR, methylation, GLC-MS, NMR-2D, SDS-PAGE, sugar analysis, GLC, mild acid hydrolysis, NMR-1D
  
   
  
  Azorhizobium caulinodans HAMBI 216
  CSDB ID 27368 (all data & tools)

Show legend Show as text

Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_1394181

• Article ID: 4871
  Zamlynska K, Komaniecka I, Turska-Szewczuk A, Pac M, Choma A "The O-specific polysaccharides from Phyllobacterium trifolii PETP02(T) LPS contain 3-C-methyl-D-rhamnose" - Carbohydrate Research 409 (2015) 25-29
  

  The O-specific polysaccharides of Phyllobacterium trifolii PETP02(T), a microsymbiont of Trifolium pratense, were obtained by mild acid hydrolysis of the lipopolysaccharide and studied by chemical analyses, mass spectrometry, and (1)H and (13)C NMR spectroscopy, including homonuclear ((1)H,(1)H DQF-COSY, TOCSY, NOESY) and heteronuclear ((1)H,(13)C HSQC, HMQC, HMBC) experiments. It was revealed that α-D-rhamnose and β-3-C-methyl-D-rhamnose (evalose) were the only components of two identified O-polysaccharides. The major O-polysaccharide was found to consist of linear hexasaccharide repeating units, while the other minor one, is composed of disaccharide repeats. The following structures of two O-polysaccharides were established: →2)-β-D-Rhap3CMe-(1→3)-α-D-Rhap-(1→3)-α-D-Rhap-(1→2)-β-D-Rhap3CMe-(1→3)-α-D-Rhap-(1→2)-α-D-Rhap-(1→ and →2)-β-D-Rhap3CMe-(1→3)-α-D-Rhap-(1→.

  Lipopolysaccharide, structure, rhamnose, O-specific polysaccharides, 3-C-methyl-D-rhamnose, evalose, 3-C-Methylrhamnose, Phyllobacterium trifolii

  NCBI PubMed ID: 25917130
  Publication DOI: 10.1016/j.carres.2015.02.013
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: adam.choma@poczta.umcs.lublin.pl
  Institutions: Department of Genetics and Microbiology, Maria Curie-Sklodowska University, Akademicka 19, 20-033 Lublin, Poland
  Methods: 13C NMR, 1H NMR, NMR-2D, GC-MS, SDS-PAGE, mild acid hydrolysis, GC, composition analysis, NMR-1D, GPC
  
   
  
  Phyllobacterium trifolii PETP02(T)
  CSDB ID 11230 (all data & tools)