Found 228 structures.
Displayed structures from 1 to 15
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1. Compound ID: 1020
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Subst3-(1-5)-a-D-Araf-(1-5)-Subst2-(1-5)-a-D-Araf-(1-5)-+
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b-D-Galf-(1-6)-b-D-Galf-(1-5)-b-D-Galf-(1-5)-Subst1-(1-6)-b-D-Galf-(1-5)-b-D-Galf-(1-5)-b-D-Galf-(1-5)-b-D-Galf-(1-4)-Subst4
Subst1 = galactan (ID 31427);
Subst2 = arabinan (ID 31426);
Subst3 = hexaarabinosyl motif (ID 31422);
Subst4 = linker-peptidoglycan (ID 31425) |
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Structure type: oligomer
Trivial name: galactan
Compound class: arabinogalactan
Contained glycoepitopes: IEDB_136095,IEDB_137472,IEDB_149137,IEDB_149176,IEDB_190606,IEDB_885812
The structure is contained in the following publication(s):
- Article ID: 303
Lee RE, Brennan PJ, Besra GS "Mycobacterium tuberculosis cell envelope" -
Book: Tuberculosis (series: Current Topics in Microbiology and Immunology) (1996) Vol. 215, 1-27
The mycobacterial cell wall is a complex and intriguing mixture of components which sets Mycobacterium tuberculosis apart from all other known bacterial species (Goodfellow and Minnikin 1984). To understand the M. tuberculosis cell wall, one must first consider the biology of the tubercle bacillus. Tuberculosis has long been known as a cause of morbidity and mortality worldwide. Indeed it is believed that one third of the word’s population is infected with M. tuberculosis (Sudre et al. 1992). Evidence of tuberculosis-like infections date back many thousands of years, and it is very likely that tuberculosis-related infections have plagued humankind since the dawn of civilization. M. tuberculosis is primarily an intracellular pathogen which resides within the phagolysosomes of alveolar macrophages. Perhaps as a consequence of this intracellular environment, the highly intricate features of the tubercle bacilli cell wall have undergone extensive evolutionary changes.
lipid, Mycobacteria, membrane, arabinogalactan, cell envelope, lipoarabinomannan, Mycobacterium tuberculosis, peptidoglycan
Publication DOI: 10.1007/978-3-642-80166-2_1Publisher: Berlin, Heidelberg: Springer.
Editors: Shinnick TM
Institutions: Department of Microbiology, Colorado State University, Fort Collins, CO, 80523, USA
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2. Compound ID: 2068
Structure type: oligomer
Contained glycoepitopes: IEDB_136095,IEDB_137472,IEDB_149176,IEDB_190606
The structure is contained in the following publication(s):
- Article ID: 673
Gurjar MK, Reddy LK, Hotha S "Synthesis of oligosaccharides of motifs D and E of arabinogalactan present in Mycobacterium tuberculosis" -
Journal of Organic Chemistry 66(13) (2001) 4657-4660
Syntheses of the ethyl glycosides of 5-O-(β-D-galactofuranosyl)-β-D-galactofuranose and 5-O-(α-D-arabinofuranosyl)-6-O-(β-D-galactofuranosyl)-β-D-galactofuranose present in motifs D and E of Mycobacterium tuberculosis arabinogalactan, respectively, have been presented. The pentenyl-mediated O-glycosylation reaction was utilized to obtain the disaccharide of motif D. The first coupling reaction to prepare the inner disaccharide portion of motif E was accomplished by trichloroacetamidate method while the installation of the terminal sugar by pentenyl glycosylation approach was successful.
synthesis, oligosaccharide, Oligosaccharides, motif, Mycobacterium, Mycobacteria, arabinogalactan, Mycobacterium tuberculosis, tuberculosis
NCBI PubMed ID: 11421788Journal NLM ID: 2985193RPublisher: Columbus, OH: American Chemical Society
Correspondence: gurjar@dalton.ncl.res.in
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3. Compound ID: 2660
Structure type: oligomer
Aglycon: 9-decen-1-ol
Trivial name: neoglycolipid acceptor
Contained glycoepitopes: IEDB_136095,IEDB_137472,IEDB_149176,IEDB_190606
The structure is contained in the following publication(s):
- Article ID: 908
Kremer L, Dover LG, Morehouse C, Hitchin P, Everett M, Morris HR, Dell A, Brennan PJ, McNeil MR, Flaherty C, Duncan K, Besra GS "Galactan biosynthesis in Mycobacterium tuberculosis. Identification of a bifunctional UDP-galactofuranosyltransferase" -
Journal of Biological Chemistry 276(28) (2001) 26430-26440
The cell wall of Mycobacterium tuberculosis and related genera is unique among prokaryotes, consisting of a covalently bound complex of mycolic acids, D-arabinan and D-galactan, which is linked to peptidoglycan via a special linkage unit consisting of Rhap-(1→3)-GlcNAc-P. Information concerning the biosynthesis of this entire polymer is now emerging with the promise of new drug targets against tuberculosis. Accordingly, we have developed a galactosyltransferase assay that utilizes the disaccharide neoglycolipid acceptors β-D-Galf-(1→5)-β-D-Galf-O-C(10:1) and β-D-Galf-(1→6)-β-D-Galf-O-C(10:1), with UDP-Gal in conjunction with isolated membranes. Chemical analysis of the subsequent reaction products established that the enzymatically synthesized products contained both β-D-Galf linkages ((1→5) and (1→6)) found within the mycobacterial cell, as well as in an alternating (1→5) and (1→6) fashion consistent with the established structure of the cell wall. Furthermore, through a detailed examination of the M. tuberculosis genome, we have shown that the gene product of Rv3808c, now termed glfT, is a novel UDP- galactofuranosyltransferase. This enzyme possesses dual functionality in performing both (1→5) and (1→6) galactofuranosyltransferase reactions with the above neoglycolipid acceptors, using membranes isolated from the heterologous host Escherichia coli expressing Rv3808c. Thus, at a biochemical and genetic level, the polymerization of the galactan region of the mycolyl-arabinogalactan complex has been defined, allowing the possibility of further studies toward substrate recognition and catalysis and assay development. Ultimately, this may also lead to a more rational approach to drug design to be explored in the context of mycobacterial infections.
structure, gene, cell wall, Substrate Specificity, D-galactan, Galactosyltransferases, Mycobacterium tuberculosis, tuberculosis, mycolic acid, neoglycolipid
NCBI PubMed ID: 11304545Publication DOI: 10.1074/jbc.M102022200Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Correspondence: g.s.besra@newcastle.ac.uk
Institutions: Department of Microbiology and Immunology, University of Newcastle upon Tyne, Newcastle upon Tyne, NE2 4HH, United Kingdom
Methods: methylation, FAB-MS
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4. Compound ID: 2661
Structure type: oligomer
Aglycon: 9-decen-1-ol
Contained glycoepitopes: IEDB_136095,IEDB_137472,IEDB_149176,IEDB_190606,IEDB_885812
The structure is contained in the following publication(s):
- Article ID: 908
Kremer L, Dover LG, Morehouse C, Hitchin P, Everett M, Morris HR, Dell A, Brennan PJ, McNeil MR, Flaherty C, Duncan K, Besra GS "Galactan biosynthesis in Mycobacterium tuberculosis. Identification of a bifunctional UDP-galactofuranosyltransferase" -
Journal of Biological Chemistry 276(28) (2001) 26430-26440
The cell wall of Mycobacterium tuberculosis and related genera is unique among prokaryotes, consisting of a covalently bound complex of mycolic acids, D-arabinan and D-galactan, which is linked to peptidoglycan via a special linkage unit consisting of Rhap-(1→3)-GlcNAc-P. Information concerning the biosynthesis of this entire polymer is now emerging with the promise of new drug targets against tuberculosis. Accordingly, we have developed a galactosyltransferase assay that utilizes the disaccharide neoglycolipid acceptors β-D-Galf-(1→5)-β-D-Galf-O-C(10:1) and β-D-Galf-(1→6)-β-D-Galf-O-C(10:1), with UDP-Gal in conjunction with isolated membranes. Chemical analysis of the subsequent reaction products established that the enzymatically synthesized products contained both β-D-Galf linkages ((1→5) and (1→6)) found within the mycobacterial cell, as well as in an alternating (1→5) and (1→6) fashion consistent with the established structure of the cell wall. Furthermore, through a detailed examination of the M. tuberculosis genome, we have shown that the gene product of Rv3808c, now termed glfT, is a novel UDP- galactofuranosyltransferase. This enzyme possesses dual functionality in performing both (1→5) and (1→6) galactofuranosyltransferase reactions with the above neoglycolipid acceptors, using membranes isolated from the heterologous host Escherichia coli expressing Rv3808c. Thus, at a biochemical and genetic level, the polymerization of the galactan region of the mycolyl-arabinogalactan complex has been defined, allowing the possibility of further studies toward substrate recognition and catalysis and assay development. Ultimately, this may also lead to a more rational approach to drug design to be explored in the context of mycobacterial infections.
structure, gene, cell wall, Substrate Specificity, D-galactan, Galactosyltransferases, Mycobacterium tuberculosis, tuberculosis, mycolic acid, neoglycolipid
NCBI PubMed ID: 11304545Publication DOI: 10.1074/jbc.M102022200Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Correspondence: g.s.besra@newcastle.ac.uk
Institutions: Department of Microbiology and Immunology, University of Newcastle upon Tyne, Newcastle upon Tyne, NE2 4HH, United Kingdom
Methods: methylation, FAB-MS
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5. Compound ID: 2662
Structure type: oligomer
Aglycon: 9-decen-1-ol
Contained glycoepitopes: IEDB_136095,IEDB_137472,IEDB_149176,IEDB_190606,IEDB_885812
The structure is contained in the following publication(s):
- Article ID: 908
Kremer L, Dover LG, Morehouse C, Hitchin P, Everett M, Morris HR, Dell A, Brennan PJ, McNeil MR, Flaherty C, Duncan K, Besra GS "Galactan biosynthesis in Mycobacterium tuberculosis. Identification of a bifunctional UDP-galactofuranosyltransferase" -
Journal of Biological Chemistry 276(28) (2001) 26430-26440
The cell wall of Mycobacterium tuberculosis and related genera is unique among prokaryotes, consisting of a covalently bound complex of mycolic acids, D-arabinan and D-galactan, which is linked to peptidoglycan via a special linkage unit consisting of Rhap-(1→3)-GlcNAc-P. Information concerning the biosynthesis of this entire polymer is now emerging with the promise of new drug targets against tuberculosis. Accordingly, we have developed a galactosyltransferase assay that utilizes the disaccharide neoglycolipid acceptors β-D-Galf-(1→5)-β-D-Galf-O-C(10:1) and β-D-Galf-(1→6)-β-D-Galf-O-C(10:1), with UDP-Gal in conjunction with isolated membranes. Chemical analysis of the subsequent reaction products established that the enzymatically synthesized products contained both β-D-Galf linkages ((1→5) and (1→6)) found within the mycobacterial cell, as well as in an alternating (1→5) and (1→6) fashion consistent with the established structure of the cell wall. Furthermore, through a detailed examination of the M. tuberculosis genome, we have shown that the gene product of Rv3808c, now termed glfT, is a novel UDP- galactofuranosyltransferase. This enzyme possesses dual functionality in performing both (1→5) and (1→6) galactofuranosyltransferase reactions with the above neoglycolipid acceptors, using membranes isolated from the heterologous host Escherichia coli expressing Rv3808c. Thus, at a biochemical and genetic level, the polymerization of the galactan region of the mycolyl-arabinogalactan complex has been defined, allowing the possibility of further studies toward substrate recognition and catalysis and assay development. Ultimately, this may also lead to a more rational approach to drug design to be explored in the context of mycobacterial infections.
structure, gene, cell wall, Substrate Specificity, D-galactan, Galactosyltransferases, Mycobacterium tuberculosis, tuberculosis, mycolic acid, neoglycolipid
NCBI PubMed ID: 11304545Publication DOI: 10.1074/jbc.M102022200Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Correspondence: g.s.besra@newcastle.ac.uk
Institutions: Department of Microbiology and Immunology, University of Newcastle upon Tyne, Newcastle upon Tyne, NE2 4HH, United Kingdom
Methods: methylation, FAB-MS
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6. Compound ID: 2663
|
b-D-Galf-(1-6)-b-D-Galf-(1-5)-b-D-Galf-(1-6)-b-D-Galf-(1--/9-decen-1-ol/ |
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Structure type: oligomer
Aglycon: 9-decen-1-ol
Contained glycoepitopes: IEDB_136095,IEDB_137472,IEDB_149176,IEDB_190606,IEDB_885812
The structure is contained in the following publication(s):
- Article ID: 908
Kremer L, Dover LG, Morehouse C, Hitchin P, Everett M, Morris HR, Dell A, Brennan PJ, McNeil MR, Flaherty C, Duncan K, Besra GS "Galactan biosynthesis in Mycobacterium tuberculosis. Identification of a bifunctional UDP-galactofuranosyltransferase" -
Journal of Biological Chemistry 276(28) (2001) 26430-26440
The cell wall of Mycobacterium tuberculosis and related genera is unique among prokaryotes, consisting of a covalently bound complex of mycolic acids, D-arabinan and D-galactan, which is linked to peptidoglycan via a special linkage unit consisting of Rhap-(1→3)-GlcNAc-P. Information concerning the biosynthesis of this entire polymer is now emerging with the promise of new drug targets against tuberculosis. Accordingly, we have developed a galactosyltransferase assay that utilizes the disaccharide neoglycolipid acceptors β-D-Galf-(1→5)-β-D-Galf-O-C(10:1) and β-D-Galf-(1→6)-β-D-Galf-O-C(10:1), with UDP-Gal in conjunction with isolated membranes. Chemical analysis of the subsequent reaction products established that the enzymatically synthesized products contained both β-D-Galf linkages ((1→5) and (1→6)) found within the mycobacterial cell, as well as in an alternating (1→5) and (1→6) fashion consistent with the established structure of the cell wall. Furthermore, through a detailed examination of the M. tuberculosis genome, we have shown that the gene product of Rv3808c, now termed glfT, is a novel UDP- galactofuranosyltransferase. This enzyme possesses dual functionality in performing both (1→5) and (1→6) galactofuranosyltransferase reactions with the above neoglycolipid acceptors, using membranes isolated from the heterologous host Escherichia coli expressing Rv3808c. Thus, at a biochemical and genetic level, the polymerization of the galactan region of the mycolyl-arabinogalactan complex has been defined, allowing the possibility of further studies toward substrate recognition and catalysis and assay development. Ultimately, this may also lead to a more rational approach to drug design to be explored in the context of mycobacterial infections.
structure, gene, cell wall, Substrate Specificity, D-galactan, Galactosyltransferases, Mycobacterium tuberculosis, tuberculosis, mycolic acid, neoglycolipid
NCBI PubMed ID: 11304545Publication DOI: 10.1074/jbc.M102022200Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Correspondence: g.s.besra@newcastle.ac.uk
Institutions: Department of Microbiology and Immunology, University of Newcastle upon Tyne, Newcastle upon Tyne, NE2 4HH, United Kingdom
Methods: methylation, FAB-MS
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7. Compound ID: 2912
Structure type: polymer chemical repeating unit
Trivial name: galactan
Compound class: EPS, O-polysaccharide, O-antigen, cell wall polysaccharide
Contained glycoepitopes: IEDB_136095,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_149176,IEDB_151528,IEDB_190606,IEDB_885812,SB_7
The structure is contained in the following publication(s):
- Article ID: 1041
Nagaoka M, Hashimoto S, Shibata H, Kimura I, Kimura K, Sawada H, Yokokura T "Structure of a galactan from cell walls of Bifidobacterium catenulatum YIT4016" -
Carbohydrate Research 281(2) (1996) 285-291
A structural study was carried out on a galactose-rich polysaccharide fraction isolated from cell walls of Bifidobacterium catenulatum YIT4016 after N-acetylmuramidase digestion. The polysaccharide contained galactose and glucosamine in a molar ratio of 16.9:1.0. Data obtained by 13C NMR spectroscopy showed that the backbone chain of this polysaccharide is composed of galactofuranose residues, while the branches consist of galactopyranosyl residues. Furthermore, the data obtained from NaIO4 oxidation, partial methanolysis and methylation analysis indicated that this polysaccharide consists of a trisaccharide repeating unit having the following structure: [sequence: see text]
structure, polysaccharide, cell, cell wall, Bifidobacterium, Galactan, D-galactose, furanose
NCBI PubMed ID: 8721149Journal NLM ID: 0043535Publisher: Elsevier
Institutions: Yakult Central Institute for Microbiological Research, Kunitachi-shi,Tokyo 186, Japan.
Methods: methylation, NMR-2D, partial acid hydrolysis, NMR
- Article ID: 1778
Knirel YA, Kochetkov NK "The structure of lipopolysaccharides of gram-negative bacteria. III. The structure of O-antigens: A review" -
Biochemistry (Moscow) 59(12) (1994) 1325-1383
This review summarizes data on the composition and structure of the O-antigens, the polysaccharide chains of the outer-membrane lipopolysaccharides (LPS) of Gram-negative bacteria defining the immunospecificity of these microbial cells. Special reference is given to some structural features of the O-antigens, such as the presence of unique monosaccharides and noncarbohydrate components, masked regularity, and the occurrence in one microorganism of LPS with structurally different polysaccharide chains. Antigenic relationships between microorganisms belonging to different taxonomic groups are discussed.
structure, O-antigen, chemical composition, bacterial lipopolysaccharides, Salmonella livingstone C1
NCBI PubMed ID: 7533007Journal NLM ID: 0376536Publisher: Nauka/Interperiodica
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
- Article ID: 1931
Beynon LM, Perry MB, Richards JC "Structure of the O-antigen of Actinobacillus pleuropneumoniae serotype 12 lipopolysaccharide" -
Canadian Journal of Chemistry 69(2) (1991) 218-224
The structure of the O-antigen of Actinobacillus pleuropneumoniae serotype 12 was determined by 1D and 2D NMR spectroscopic methods, methylation analysis, and partial hydrolytic degradation. The O-polysaccharide was shown to consist of a trisaccharide repeating unit having the structure [formula in text].
Lipopolysaccharide, antigen, polysaccharide, Actinobacillus pleuropneumoniae
Publication DOI: 10.1139/v91-035Journal NLM ID: 0372705Publisher: National Research Council of Canada Canada
Institutions: Institute for Biological Sciences, National Research Council of Canada, Ottawa, Ontario
Methods: 13C NMR, 1H NMR, methylation, GLC-MS, gel filtration, NMR-2D, sugar analysis, TLC, HF treatment
- 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_3Publisher: 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: 4434
Perry MB, Altman E, Brisson JR "Structural caharacteristics of the antigenic capsular polysaccharides and lipopolysaccharides involved in the serological classification of Actinobacillus (Haemophilus) pleuropneumoniae strains" -
Serodiagnosis and Immunotherapy in Infectious Disease 4 (1990) 299-308
The detailed structures of the specific capsular polysaccharides and cellular lipopolysaccharides of the 12 known serotypes of Actinobacillus (Haemophilus) pleuropneumoniae are presented and their serological relationships are discussed together with their significance in the control of swine pleuropneumonia.
lipopolysaccharides, polysaccharides, capsules, Actinobacillus (Haemophilus) pleuropneumoniae
Publication DOI: 10.1016/0888-0786(90)90018-JJournal NLM ID: 8707525Publisher: London; Orlando: Academic Press
Institutions: Institute for Biological Sciences, National Research Council Canada, Ottawa, Ont., Canada K1A 0R6
Methods: serological methods
- Article ID: 4682
Hidalgo-Cantabrana C, Sanchez B, Milani C, Ventura M, Margolles A, Ruas-Madiedo P "Genomic Overview and Biological Functions of Exopolysaccharide Biosynthesis in Bifidobacterium spp" -
Applied and Environmental Microbiology 80(1) (2014) 9-18
For many years, bacterial exopolysaccharides (EPS) have received considerable scientific attention, mainly due to their contribution to biofilm formation and, above all, because EPS are potential virulence factors. In recent times, interest in EPS research has enjoyed a welcome boost thanks to the discovery of their ability to mediate communication processes with their surrounding environment and to their contribution to host health maintenance. In this review, we provide a fresh perspective on the genetics and activity of these polymers in members of the Bifidobacterium genus, a common gut inhabitant of humans and animals that has been associated with several health-promoting effects. Bifidobacteria can use EPS to protect themselves against the harsh conditions of the gastrointestinal tract, thus improving their persistence in the host. Indeed, the relevant function of EPS for bifidobacteria is underlined by the fact that most genomes sequenced until now contain genes related to EPS biosynthesis. A high interspecies variability in the number of genes and structural organization is denoted among species/subspecies; thus, eps clusters in this genus do not display a consensus genetic architecture. Their different G+C content compared to that of the whole genome suggests that eps genes have been acquired by horizontal transfer. From the host perspective, EPS-producing bifidobacteria are able to trigger both innate and adaptive immune responses, and they are able to modulate the composition and activity of the gut microbiota. Thus, these polymers seem to be critical in understanding the physiology of bifidobacteria and their interaction with the host.
cluster, exopolysaccharide, Bifidobacterium, immune response, virulence factor, Biofilm, Bacterial exopolysaccharides, EPS biosynthesis
NCBI PubMed ID: 24123746Publication DOI: 10.1128/AEM.02977-13Journal NLM ID: 7605801Publisher: American Society for Microbiology
Correspondence: ruas-madiedo@ipla.csic.es
Institutions: Department of Microbiology and Biochemistry of Dairy Products, Instituto de Productos Lacteos de Asturias-Consejo Superior de Investigaciones Cientificas (IPLA-CSIC), Asturias, Spain
- Article ID: 5832
Pyclik M, Srutkova D, Schwarzer M, Gorska S "Bifidobacteria cell wall-derived exo-polysaccharides, lipoteichoic acids, peptidoglycans, polar lipids and proteins - their chemical structure and biological attributes" -
International Journal of Biological Macromolecules 147 (2020) 333-349
A variety of health benefits has been documented to be associated with the consumption of probiotic bacteria, namely bifidobacteria and lactobacilli. Thanks to the scientific advances in recent years we are beginning to understand the molecular mechanisms by which bacteria in general and probiotic bacteria in particular act as host physiology and immune system modulators. More recently, the focus has shifted from live bacteria towards bacteria-derived defined molecules, so called postbiotics. These molecules may represent safer alternative compared to the live bacteria while retaining the desired effects on the host. The excellent source of effector macromolecules is the bacterial envelope. It contains compounds that are pivotal in the adhesion phenomenon, provide direct bacteria-to-host signaling capacity and the associated physiological impact and immunomodulatory properties of bacteria. Here we comprehensively review the structure and biological role of Bifidobacterium surface and cell wall molecules: exopolysaccharides, cell wall polysaccharides, lipoteichoic acids, polar lipids, peptidoglycans and proteins. We discuss their involvement in direct signaling to the host cells and their described immunomodulatory effects.
exopolysaccharide, Bacterial antigens, Bifidobacterium, peptidoglycan, lipoteichoic acid, probiotics
NCBI PubMed ID: 31899242Publication DOI: 10.1016/j.ijbiomac.2019.12.227Journal NLM ID: 7909578Publisher: Butterworth-Heinemann
Correspondence: schwarzer@biomed.cas.cz; sabina.gorska@hirszfeld.pl
Institutions: Laboratory of Microbiome Immunobiology, Hirszfeld Institute of Immunology and Experimental Therapy, Polish Academy of Sciences, Wroclaw, Poland, Laboratory of Gnotobiology, Institute of Microbiology of the Czech Academy of Sciences, Novy Hradek, Czech Republic
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8. Compound ID: 3011
Structure type: polymer chemical repeating unit
; n=15
Trivial name: galactofuran
Contained glycoepitopes: IEDB_136095,IEDB_137472,IEDB_149176,IEDB_190606,IEDB_885812
The structure is contained in the following publication(s):
- Article ID: 1077
Pan F, Jackson M, Ma Y, McNeil M "Cell wall core galactofuran synthesis is essential for growth of mycobacteria" -
Journal of Bacteriology 183(13) (2001) 3991-3998
The mycobacterial cell wall core consists of an outer lipid (mycolic acid) layer attached to peptidoglycan via a galactofuranosyl-containing polysaccharide, arabinogalactan. This structural arrangement strongly suggests that galactofuranosyl residues are essential for the growth and viability of mycobacteria. Galactofuranosyl residues are formed in nature by a ring contraction of UDP-galactopyranose to UDP- galactofuranose catalyzed by the enzyme UDP-galactopyranose mutase (Glf). In Mycobacterium tuberculosis the glf gene overlaps, by 1 nucleotide, a gene, Rv3808c, that has been shown to encode a galactofuranosyl transferase. We demonstrate here that glf can be knocked out in Mycobacterium smegmatis by allelic replacement only in the presence of two rescue plasmids carrying functional copies of glf and Rv3808c. The glf rescue plasmid was designed with a temperature- sensitive origin of replication and the M. smegmatis glf knockout mutant is unable to grow at the higher temperature at which the glf- containing rescue plasmid is lost. In a separate experiment, the Rv3808c rescue plasmid was designed with a temperature-sensitive origin of replication and the glf-bearing plasmid was designed with a normal original of replication; this strain was also unable to grow at the nonpermissive temperature. Thus, both glf and Rv3808c are essential for growth. These findings and the fact that galactofuranosyl residues are not found in humans supports the development of UDP-galactopyranose mutase and galactofuranosyl transferase as important targets for the development of new antituberculosis drugs
biosynthesis, synthesis, core, functional, gene, human, microbiology, strain, structural, polysaccharide, cell, acid, transferase, lipid, mutant, cell wall, plasmid, galactofuranose, Mycobacterium, enzyme, Mycobacteria, arabinogalactan, Mycobacterium tuberculosis, peptidoglycan, Mycobacterium smegmatis, tuberculosis, ring, origin, Plasmids, sensitive, mycolic acid, growth, temperature, target, development, drug, drugs, layer
NCBI PubMed ID: 11395463Journal NLM ID: 2985120RPublisher: American Society for Microbiology
Correspondence: mmcneil@cvmbs.colostate.edu
Institutions: Department of Microbiology, Colorado State University, Fort Collins, Colorado 80523, USA
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9. Compound ID: 3323
Structure type: polymer chemical repeating unit
; n=6
Compound class: teichoic acid
Contained glycoepitopes: IEDB_136095,IEDB_137472,IEDB_149176,IEDB_190606
The structure is contained in the following publication(s):
- Article ID: 1225
Shashkov AS, Tul'skaya EM, Evtushenko LI, Grachev AA, Naumova IB "Structure of a teichoic acid from Nocardioides luteus VKM Ac-1246T cell wall" -
Biochemistry (Moscow) 65(4) (2000) 509-514
structure, cell, acid, phosphate, cell wall, PAGE, ribitol, teichoic acid, glycerol, Nocardia
Journal NLM ID: 0376536Publisher: Nauka/Interperiodica
Institutions: Institute of Biochemistry and Physiology of Microorganisms, Russian Academy of Sciences,Pushchino,Russia
Methods: NMR
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10. Compound ID: 3371
|
a-D-Rhap-(1-3)-a-L-FucpNAc-(1-3)-b-D-GlcpNAc-(1-2)-+
|
-3)-b-D-Galf-(1-6)-b-D-Galf-(1-3)-b-D-Galf-(1-6)-b-D-Galf-(1- |
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Structure type: polymer chemical repeating unit
Compound class: cell wall polysaccharide
Contained glycoepitopes: IEDB_135813,IEDB_136095,IEDB_137340,IEDB_137472,IEDB_1394181,IEDB_141807,IEDB_149176,IEDB_151531,IEDB_190606
The structure is contained in the following publication(s):
- Article ID: 1244
Sorum U, Robertsen B, Kenne L "Structural studies of the major polysaccharide in the cell wall of Renibacterium salmoninarum" -
Carbohydrate Research 306(1-2) (1998) 305-314
The galactose-rich polysaccharide (GPS) in the cell wall of the Gram-positive bacterium Renibacterium salmoninarum, the causative agent in of bacterial kidney disease (BKD) of salmonids, has been studied by sugar and methylation analysis, partial acid hydrolysis, Smith degradation, FABMS, and 1H and 13C NMR spectroscopy. The data show that the GPS has a heptasaccharide repeating unit with the following structure: α-D-Rhap-(1→3)-α-L-FucpNAc-(1→)-β-D-GlcpNAc 1 decreases 2 →3)-β-D-Galf-(1→6)-β-D-Galf-(1→3)-β-D-Galf-(1→6)-β-D-Galf-(1→.
NMR, structure, cell wall polysaccharide, Renibacterium salmoninarum
NCBI PubMed ID: 9691455Publication DOI: 10.1016/s0008-6215(97)10071-4Journal NLM ID: 0043535Publisher: Elsevier
Institutions: Department of Marine Biochemistry, The Norwegian College of Fishery Science, University of Tromsø, N-9037 Tromsø, Norway, Department of Chemistry, Swedish University of Agricultural Sciences, Box 7015, S-750 07 Uppsala, Sweden
Methods: 13C NMR, 1H NMR, methylation, FAB-MS, partial acid hydrolysis, Smith degradation
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11. Compound ID: 3441
Structure type: polymer chemical repeating unit
Trivial name: SP-PG
Contained glycoepitopes: IEDB_136095,IEDB_137472,IEDB_142488,IEDB_146664,IEDB_149176,IEDB_190606,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 1290
Yamazaki K, Inukai K, Suzuki M, Kuga H, Korenaga H "Structural studies on a sulfated polysaccharide from an Arthrobacter sp. by NMR spectroscopy and methylation analysis" -
Carbohydrate Research 305(2) (1997) 253-260
Structural characterization of a sulfated polysaccharide peptidoglycan complex (SP-PG) from an Arthrobacter sp. was performed by NMR spectroscopy and methylation analysis. In order to simplify the analyses, the desulfated SP-PG was used. NMR spectroscopy revealed the presence of a trisaccharide repeating unit and a disaccharide repeating unit. The trisaccharide unit was composed of two galactofuranosides and one glucopyranoside, and the disaccharide unit was of two galactopyranosides, as shown below. The methylation analysis showed that the polysaccharide consists mainly of a 4-linked galactopyranoside, a 6-linked galactopyranoside, a 6-linked galactofuranoside, a 2,6-linked galactofuranoside, a terminal galactopyranoside and a terminal glucopyranoside. These findings confirmed the structure indicated by the NMR spectroscopy. The repeating units determined in this study are novel
methylation analysis, cell wall, 2D NMR, Arthrobacter sp., Sulfated glucogalactan
NCBI PubMed ID: 9581278Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: vamaz33x@daiichipharm.co.jp
Institutions: Basic Technology Research Laboratory, Daiichi Pharmaceutical, 16-13, Kitakasai l-Chome,Edogawa-ku, Tokyo 134, Japan, Drug Metabolism and Analytical Chemistry, Research Laboratory, Daiichi Pharmaceutical, 16-13, Kitakasai 1-Chome, Edogawa-ku, Tokyo 134, Japan, New Product Research Laboratory, IV, Daiichi Pharmaceutical, 16-13, Kitakasai l-Chome, Edogawa-ku, Tokyo 134, Japan
Methods: methylation, NMR-2D, NMR
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12. Compound ID: 3713
|
-1)-D-Rib-ol-(5--P--6)--b-D-Galf-(1-3)-b-D-Galp-(1-6)-b-D-Galf-(1-6)-b-D-Galf2Ac-(1-3)-a-D-Galp-(1- |
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Structure type: polymer chemical repeating unit
Contained glycoepitopes: IEDB_114703,IEDB_136044,IEDB_136095,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_149176,IEDB_151528,IEDB_190606,IEDB_591403,SB_165,SB_166,SB_187,SB_195,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 1402
Cisar JO, Sandberg AL, Abeygunawardana C, Reddy GP, Bush CA "Lectin recognition of host-like saccharide motifs in streptococcal cell wall polysaccharides" -
Glycobiology 5 (1995) 655-662
Viridans streptococci that participate in the microbial colonization of teeth have cell wall polysaccharides composed of linear phosphodiester-linked hexa- or heptasaccharide repeating units, each containing a host-like disaccharide motif, either Gal β1→3 GalNAc or GalNAc β1→3 Gal. Whereas strains with GalNAc β1→ Gal-containing polysaccharides co-aggregated with streptococci that possess GalNAc-sensitive lectins, strains with either host-like motif co-aggregated with Actinomyces spp. The latter interactions reflected the specificity of Actinomyces spp. lectins for common features of Gal β1→3 GalNAc and GalNAc β1→3 Gal. Thus, α-linked glycosides of both disaccharides were much more potent inhibitors of co-aggregation than Gal or GalNAc. Six non-bacterial lectins also reacted with the streptococcal polysaccharides. In general, precipitation of each lectin with each polysaccharide involved binding of Gal or GalNAc within the host-like motifs, but not saccharides outside these regions. The lectins of Ricinus communis, Abrus precatorius, Codium fragile and Agaricus bisporus were most reactive with the Gal β1→3 GalNAc-containing polysaccharides, the Wisteria floribunda lectin with the GalNAc β1→3 Gal-containing polysaccharides and the Bauhinia purpurea lectin with polysaccharides containing either disaccharide. Thus, lectin recognition of the streptococcal cell wall polysaccharides involved either the common or specific sides of the Gal β1→3 GalNAc and GalNAc β1→3 Gal motifs present within these molecules.
lectins, bacterial adhesins, cellular recognition, microbial colonization, streptococcal polysaccharides
NCBI PubMed ID: 8608267Publication DOI: 10.1093/glycob/5.7.655Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Institutions: Laboratory of Microbial Ecology, National Institute of Dental Research, National Institutes of Health, Bethesda, MD, USA
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13. Compound ID: 3761
|
/Variants 0/-+
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S-5)-+ |
| |
b-D-Glcp-(1-2)-+ | |
| | |
-6)-b-D-Galf-(1-6)-b-D-Galf-(1-
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S-3)-+
/Variants 0/ is:
S-3)-
OR (exclusively)
S-2)- |
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Structure type: polymer chemical repeating unit
Trivial name: sulfated polysaccharide-peptidoglycan complex (SP-PG)
Contained glycoepitopes: IEDB_136095,IEDB_137472,IEDB_142488,IEDB_146664,IEDB_149176,IEDB_190606,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 1434
Yamazaki K, Suzuki M, Inukai K, Kuga H, Korenaga H "Structural study on a sulfated polysaccharide-peptidoglycan complex produced by Arthrobacter sp." -
Bioscience, Biotechnology, and Biochemistry 62(11) (1998) 2138-2144
The structure of a sulfated polysaccharide-peptidoglycan complex (SP-PG) produced by Arthrobacter sp. was analyzed by NMR spectroscopy. In addition, oligosaccharide fragments of the SP-PG-L obtained by HF degradation were analyzed by NMR spectroscopy. These findings indicated that the sulfated polysaccharide (SP) contains a repeating unit composed of two galactofuranosides and a glucopyranoside. The main chain of the trisaccharide is [→6)-β-D-Galf(1→6)-β-D-Galf(1→ ln, with β-D-Glcp linked to one of the Galfs through a (1→2) linkage. The sulfated positions of the trisaccharide were identified as C-3 and C-5 of the β-glucosylated Galf residues, and C-2 or C-3 of the other Galf residue.
structural, complex, NMR spectroscopy, structural studies, sulfated, Arthrobacter, Arthrobacter sp., glucogalactan, HF degradation, sulfated polysaccharide
NCBI PubMed ID: 9972234Journal NLM ID: 9205717Publisher: Japan Society for Bioscience, Biotechnology, and Agrochemistry
Correspondence: yamaz33x@daiichipharm.co.jp
Institutions: Basic Technology Research Laboratory, Daiichi Pharmaceutical Co., Ltd., Tokyo, Japan
Methods: methylation, NMR-2D, NMR, HF solvolysis
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14. Compound ID: 4342
|
b-D-Galf-(1-6)-{{{-b-D-Galf-(1-5)-b-D-Galf-(1-6)-}}}+
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Mycolic-(1-5)-+ |
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Mycolic-(1-5)-b-D-Araf-(1-2)-a-D-Araf-(1-5)-+ |
| |
Mycolic-(1-5)-+ | {{{-a-D-Araf-(1-5)-}}}/n=7/-a-D-Araf-(1-3)-+ |
| | | |
Mycolic-(1-5)-b-D-Araf-(1-2)-a-D-Araf-(1-3)-a-D-Araf-(1-5)-{{{-a-D-Araf-(1-5)-}}}a-D-Araf-(1-5)-a-D-Araf-(1-5)-{{{-a-D-Araf-(1-5)-}}}a-D-Araf-(1-5)-b-D-Galf-(1-5)-{{{-b-D-Galf-(1-6)-b-D-Galf-(1-5)-}}}/n=3/-a-D-Galf-(1-4)-b-L-Rhap-(1-4)-a-D-GlcpNAc-(1---P---/peptidoglycan/ |
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Structure type: oligomer
Aglycon: peptidoglycan
Trivial name: arabinogalactan
Contained glycoepitopes: IEDB_136095,IEDB_137340,IEDB_137472,IEDB_141807,IEDB_149176,IEDB_150077,IEDB_151531,IEDB_159255,IEDB_190606,IEDB_225177,IEDB_885812,IEDB_885823
The structure is contained in the following publication(s):
- Article ID: 1629
Li W, Chatterjee D, Lee RE "Rapid structural characterization of the arabinogalactan and lipoarabinomannan in live mycobacterial cells using 2D and 3D HR-MAS NMR: structural changes in the arabinan due to ethambutol treatment and gene mutation are observed" -
Glycobiology 15(2) (2005) 139-151
Mycobacteria possess a unique, highly evolved, carbohydrate- and lipid-rich cell wall that is believed to be important for their survival in hostile environments. Until now, our understanding of mycobacterial cell wall structure has been based upon destructive isolation and fragmentation of individual cell wall components. This study describes the observation of the major cell wall structures in live, intact mycobacteria using 2D and 3D high-resolution magic-angle spinning (HR-MAS) nuclear magnetic resonance (NMR). As little as 20 mg (wet weight) of [13C]-enriched cells were required to produce a whole-cell spectra in which discrete cross-peaks corresponding to specific cell wall components could be identified. The most abundant signals of the arabinogalactan (AG) and lipoarabinomannan (LAM) were assigned in the HR-MAS NMR spectra by comparing the 2D and 3D NMR whole-cell spectra with the spectra of purified cellular components. This study confirmed that the structures of the AG and LAM moieties in the cell wall of live mycobacteria are consistent with structural reports in the literature, which were obtained via degradative analysis. Most important, by using intact cells it was possible to directly demonstrate the effects of ethambutol on the mycobacterial cell wall polysaccharides, characterize the effects of embB gene knockout in the M. smegmatis ∆embB mutant, and observe differences in the cell wall structures of two mycobacterial species (M. bovis BCG and M. smegmatis.) Herein, we show that HR-MAS NMR is a powerful, rapid, nondestructive technique to monitor changes in the complex, carbohydrate-rich cell wall of live mycobacterial cells.
Mycobacteria, arabinogalactan, lipoarabinomannan, Mycobacterium smegmatis, HR-MAS NMR, HCCH-TOCSY, Mycobacterium bovis, mycolyl arabinogalactanstructure
NCBI PubMed ID: 15371346Publication DOI: 10.1093/glycob/cwh150Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Correspondence: relee@utmem.edu
Institutions: Department of Pharmaceutical Sciences, University of Tennessee Health Science Center, 847 Monroe Ave. Rm. 327, Memphis, TN 38163, USA
Methods: NMR
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15. Compound ID: 4397
Structure type: polymer chemical repeating unit
Trivial name: galactan, galactan core of arabinogalactan
Contained glycoepitopes: IEDB_136095,IEDB_137472,IEDB_149176,IEDB_190606,IEDB_885812
The structure is contained in the following publication(s):
- Article ID: 1657
Tropis M, Lemassu A, Vincent V, Daffé M "Structural elucidation of the predominant motifs of the major cell wall arabinogalactan antigens from the borderline species Tsukamurella paurometabolum and Mycobacterium fallax" -
Glycobiology 15(7) (2005) 677-686
Tsukamurella paurometabolum and Mycobacterium fallax are members of the suprageneric actinomycete group Corynebacterineae that possesses a cell wall skeleton composed of a peptidoglycan to which an arabinogalactan is covalently attached. This polysaccharide is further modified by esterification with C60-C80 mycolic acid residues in mycobacteria and T. paurometabolum. However, M. fallax and T. paurometabolum produce polyenoic (up to six double bonds) mycolic acids whereas the most common type of mycobacterial mycolates, called alpha-mycolates, are mono- and di-enoic or -cyclopropanated mycolic acids. To determine whether this difference also applied to the structures of cell wall arabinogalactans, competitive inhibition experiments using antibodies raised against the cell wall from Mycobacterium bovis and the arabinogalactans from T. paurometabolum and M. fallax were performed. They demonstrated the structural identity between the polysaccharide of M. fallax and those of mycobacteria and showed a strong similarity between the latter polysaccharides and that of T. paurometabolum. Structural analyses of the per-O-alkylated alditol fragments derived from the polysaccharides by gas chromatography-mass spectrometry (GC-MS) and 13C nuclear magnetic resonance (NMR) spectroscopy of the intact solubilized polysaccharides demonstrated that the polysaccharides from the two species analyzed contained all the major structural features previously characterized in mycobacterial arabinogalactans. These include (1) the homogalactan of alterning 5-linked galactofuranosyl (Galf) and 6-linked Galf residues, (2) a linear 5-linked arabino furanosyl (Araf), (3) a β-Araf-(1→2)-α-Araf disaccharide branched on both position 3 and position 5 of an α-Araf unit, and (4) a 5-linked-α-Araf unit branched on both position 3 and position 5 of an α-Araf residue. The polysaccharide from T. paurometabolum possesses additional structural domains composed of a terminal (t) Araf directly linked to either a 5-linked-α-Araf or to both position 3 and position 5 of a 3,5-linked α-Araf unit. Both the remarkable similarity of arabinogalactans from Corynebacterineae and their genus- and/or species-specificities are reflected in their 13C NMR spectra that may be used as a valuable help in the identification of members of the actinomycete group
cell wall, Mycobacterium, arabinogalactan, Tsukamurella
NCBI PubMed ID: 15761023Publication DOI: 10.1093/glycob/cwi052Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Institutions: Departement Mecanismes Moleculaires des Infections Mycobacteriennes, Institut de Pharmacologie et Biologie Structurale, UMR 5089 du Centre National de la Recherche Scientifique et de l'Universite Paul Sabatier, 31077 Toulouse cedex 04, France
Methods: NMR
- Article ID: 2645
Daffé M, Brennan PJ, McNeil M "Predominant structural features of the cell wall arabinogalactan of Mycobacterium tuberculosis as revealed through characterization of oligoglycosyl alditol fragments by gas chromatography/mass spectrometry and by proton and carbon-13 NMR analyses" -
Journal of Biological Chemistry 265 (1990) 6734-6743
The peptidoglycan-bound arabinogalactan of a virulent strain of Mycobacterium tuberculosis was per-O-methylated, partially hydrolyzed with acid, and the resulting oligosaccharides reduced and O-pentadeute-rioethylated. The per-O-alkylated oligoglycosyl alditol fragments were separated by high pressure liquid chromatography and the structures of 43 of these constituents determined by 1H NMR and gas chromatography/mass spectrometry. The arabinogalactan was shown to consist of a galactan containing alternating 5-linked β-D-galactofuranosyl (Galf) and 6-linked β-D-Galf residues. The arabinan chains are attached to C-5 of some of the 6-linked Galf residues. The arabinan is comprised of at least three major structural domains. One is composed of linear 5-linked α-D-arabinofuranosyl (Araf) residues; a second consists of branched 3,5-linked α-D-Araf units substituted with 5-linked α-D-Araf residues at both branched positions. The non-reducing terminal region of the arabinan was characterized by a 3,5-linked α-D-Araf residue substituted at both branched positions with the disaccharide β-D-Araf-(1→2)-α-D-Araf. 13C NMR of intact soluble arabinogalactan established the presence of both α- and β-Araf residues in this domain. This non-reducing terminal motif apparently provides the structural basis of the dominant immunogenicity of arabinogalactan within mycobacteria. A rhamnosyl residue occupies the reducing terminus of the galactan core and may link the arabinogalactan to the peptidoglycan. Evidence is also presented for the presence of minor structural features involving terminal mannopyranosyl units. Models for most of the heteropolysaccharide are proposed which should increase our understanding of a molecule responsible for much of the immunogenicity, pathogenicity, and peculiar physical properties of the mycobacterial cell.
NCBI PubMed ID: 2108960Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Institutions: Department of Microbiology, Colorado State University, Fort Collins 80523
- Article ID: 4352
May JF, Levengood MR, Splain RA, Brown CD, Kiessling LL "A processive carbohydrate polymerase that mediates bifunctional catalysis using a single active site" -
Biochemistry 51(6) (2012) 1148-1159
Even in the absence of a template, glycosyltransferases can catalyze the synthesis of carbohydrate polymers of specific sequence. The paradigm has been that one enzyme catalyzes the formation of one type of glycosidic linkage, yet certain glycosyltransferases generate polysaccharide sequences composed of two distinct linkage types. In principle, bifunctional glycosyltransferases can possess separate active sites for each catalytic activity or one active site with dual activities. We encountered the fundamental question of one or two distinct active sites in our investigation of the galactosyltransferase GlfT2. GlfT2 catalyzes the formation of mycobacterial galactan, a critical cell-wall polymer composed of galactofuranose residues connected with alternating, regioisomeric linkages. We found that GlfT2 mediates galactan polymerization using only one active site that manifests dual regioselectivity. Structural modeling of the bifunctional glycosyltransferases hyaluronan synthase and cellulose synthase suggests that these enzymes also generate multiple glycosidic linkages using a single active site. These results highlight the versatility of glycosyltransferases for generating polysaccharides of specific sequence. We postulate that a hallmark of processive elongation of a carbohydrate polymer by a bifunctional enzyme is that one active site can give rise to two separate types of glycosidic bonds.
glycosyltransferases, Substrate Specificity, galactosyltransferase, Galactan, modeling, hyaluronan, polymerization
NCBI PubMed ID: 22217153Publication DOI: 10.1021/bi201820pJournal NLM ID: 0370623Publisher: American Chemical Society
Correspondence: kiessling@chem.wisc.edu
Institutions: Department of Biochemistry, University of Wisconsin, Madison, WI, USA
Methods: 1H NMR, PCR, SDS-PAGE, MALDI-TOF MS, genetic methods, biochemical methods, STD NMR, binding assays
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