Found 139 structures.
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1. Compound ID: 828
Structure type: oligomer
Compound class: glycolipid
Contained glycoepitopes: IEDB_128162,IEDB_128164,IEDB_134625,IEDB_136105,IEDB_137477,IEDB_142488,IEDB_146664,IEDB_225177,IEDB_885823,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 227
Wu XM, Mariño-Albernas JR, Auzanneau FI, Verez-Bencomo V, Pinto BM "Synthesis and NMR analysis of 13C-labeled oligosaccharides corresponding to the major glycolipid from Mycobacterium leprae" -
Carbohydrate Research 306(4) (1998) 493-503
An improved synthesis of propyl 4-O-(3,6-di-O-methyl-b-D-glycopyranosyl)-2,3-di-O-methyl-a-L-rhamnopyranoside, a disaccharide corresponding to the phenolic glycolipid of Mycobacterium leprae using a trichloroacetimidate as a glycosyl donor is described. The synthetic strategy is also applied to the preparation of three corresponding disaccharide analogues containing 13C-labeled methyl groups. The preparation of the trisaccharide, propyl 2-O-[4-O-93.6-di_O-methyl-b-D-glucopyranosyl)-2,3-di-O-methyl-a-L-rhamnopyranosyl]-3-O-methyl-a-L-rhamnopyranoside is also reported. The di-and tri-saccharides were characterized by 1H and 13C NMR spectroscopy.
NMR, synthesis, oligosaccharide, analysis, Oligosaccharides, Mycobacterium, Mycobacteria, glycolipid, C-13-labeled, Mycobacterium leprae, NMR analysis, oligosaccharide haptens
NCBI PubMed ID: 9679274Journal NLM ID: 0043535Publisher: Elsevier
Institutions: Department of Chemistry, Simon Fraser University, Burnaby, B.C., Canada, V5A 1S6, Laboratory for Carbohydrate Chemistry, Fucltad de Quimica, Universidad de la Habana, Centro Nacional de Biopreparados, Ciudad Habana, Cuba
Methods: chemical methods
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2. Compound ID: 829
Structure type: oligomer
Contained glycoepitopes: IEDB_128162,IEDB_128163,IEDB_128164,IEDB_131183,IEDB_133754,IEDB_134625,IEDB_136105,IEDB_137477,IEDB_142488,IEDB_146664,IEDB_225177,IEDB_885823,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 227
Wu XM, Mariño-Albernas JR, Auzanneau FI, Verez-Bencomo V, Pinto BM "Synthesis and NMR analysis of 13C-labeled oligosaccharides corresponding to the major glycolipid from Mycobacterium leprae" -
Carbohydrate Research 306(4) (1998) 493-503
An improved synthesis of propyl 4-O-(3,6-di-O-methyl-b-D-glycopyranosyl)-2,3-di-O-methyl-a-L-rhamnopyranoside, a disaccharide corresponding to the phenolic glycolipid of Mycobacterium leprae using a trichloroacetimidate as a glycosyl donor is described. The synthetic strategy is also applied to the preparation of three corresponding disaccharide analogues containing 13C-labeled methyl groups. The preparation of the trisaccharide, propyl 2-O-[4-O-93.6-di_O-methyl-b-D-glucopyranosyl)-2,3-di-O-methyl-a-L-rhamnopyranosyl]-3-O-methyl-a-L-rhamnopyranoside is also reported. The di-and tri-saccharides were characterized by 1H and 13C NMR spectroscopy.
NMR, synthesis, oligosaccharide, analysis, Oligosaccharides, Mycobacterium, Mycobacteria, glycolipid, C-13-labeled, Mycobacterium leprae, NMR analysis, oligosaccharide haptens
NCBI PubMed ID: 9679274Journal NLM ID: 0043535Publisher: Elsevier
Institutions: Department of Chemistry, Simon Fraser University, Burnaby, B.C., Canada, V5A 1S6, Laboratory for Carbohydrate Chemistry, Fucltad de Quimica, Universidad de la Habana, Centro Nacional de Biopreparados, Ciudad Habana, Cuba
Methods: chemical methods
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3. Compound ID: 1469
|
Me-3)-{{{-a-L-Rhap-(1-4)-a-D-Manp-(1-3)-}}}/n=28/-a-L-Rhap-(1-3)-a-L-Rhap-(1-3)-a-L-Rhap-(1-3)-b-D-Galp-(1-7)-Tyr |
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Structure type: oligomer
Compound class: S-layer glycoprotein
Contained glycoepitopes: IEDB_130701,IEDB_136044,IEDB_136105,IEDB_137472,IEDB_137477,IEDB_141794,IEDB_144983,IEDB_152206,IEDB_190606,IEDB_225177,IEDB_885823,IEDB_983930,SB_165,SB_166,SB_187,SB_195,SB_44,SB_67,SB_7,SB_72,SB_88
The structure is contained in the following publication(s):
- Article ID: 467
Schäffer C, Messner P "Surface-layer glycoproteins: an example for the diversity of bacterial glycosylation with promising impacts on nanobiotechnology" -
Glycobiology 14(8) (2004) 31R-42R
Bacterial cell surface layers, referred to simply as S-layers, have been described for all major phylogenetic groups of bacteria, which may indicate their pivotal role for a bacterium in its natural habitat. They have the unique ability to assemble into two-dimensional crystalline arrays that completely cover the bacterial cells. Glycosylation represents the most frequent modification of S-layer proteins. S-layer glycoproteins constitute a class of glycoconjugates first isolated in the mid-1970s, but S-layer glycoprotein research is still being regarded as an 'exotic field of glycobiology,' possibly because of its 'noneukaryotic' character. Extensive work over the past 30 years provided evidence of an enormous diversity of S-layer glycoproteins that have been created in nature over 3 billion years of prokaryotic evolution. These glycoconjugates are substantially different from eukaryotic glycoproteins, with regard to both composition and structure; nevertheless, some general structural concepts may be deduced. The awareness of the high application potential of S-layer glycoproteins, especially in combination with their intrinsic cell surface display feature, in the field of modern nanobiotechnology as a base for glycoengineering has recently led to the investigation of the S-layer protein glycosylation process at the molecular level, which has lagged behind the structural studies due to the lack of suitable molecular tools. From that work an even more interesting picture of this class of glycoconjugates is emerging. The availability of purified enzymes from S-layer glycan biosynthesis pathways exhibiting increased stabilities and/or rare sugar specificities in conjunction with preliminary genomic data on S-layer glycan biosynthesis clusters will pave the way for the rational design of S-layer neoglycoproteins.
LPS, bacterial glycosylation, genomic glycosylation loci, glycan diversity, glycoengineering, S-layer nanoglycobiology
NCBI PubMed ID: 15044388Publication DOI: 10.1093/glycob/cwh064Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Correspondence: paul.messner@boka.ac.at
Institutions: Center for NanoBiotechnology, University of Applied Life Sciences and Natural Resources, Gregor-Mendel-Strasse 33, A-1180 Wien, Austria
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4. Compound ID: 2044
|
b-L-Xylp-(1-4)-a-L-Rhap3Me-(1-3)-b-D-Galp-(1-3)-b-D-Glcp-(1-4)-a-D-Glcp-(1-1)-a-D-Glcp |
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Structure type: oligomer
Compound class: LOS
Contained glycoepitopes: IEDB_136044,IEDB_136105,IEDB_137472,IEDB_137477,IEDB_141794,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_190606,IEDB_225177,IEDB_742521,IEDB_885823,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 648
Gilleron M, Puzo G "Lipooligosaccharidic antigens from Mycobacterium kansasii and Mycobacterium gastri" -
Glycoconjugate Journal 12 (1995) 298-308
A set of Lipooligosaccharides (LOSs) has previously been characterized in M. gastri W471. The structure of the highly antigenic LOS (LOS-III) was elucidated and this molecule can unambiguously distinguish M. gastri from the opportunistic pathogen M. kansasii. In the present study, the structures of three other M. gastri W471 LOSs were determined by one-dimensional 1H NMR spectroscopy and gas liquid chromatography. They differ by the number of Xylp units and by the structure of the distal monosaccharide. The two dimensional (2D) NMR approach was successfully applied to the LOS antigen of M. kansasii to locate the acetyl and acyl substituents and to determine the anomeric configuration of the α-D-Fucp unit. The molecular specificity of anti-LOS-III antibodies was investigated and the LOS-III epitope was defined as the distal disaccharide: 3,6-dideoxy-4-C-(1,3-dimethoxy-4,5,6,7-tetrahydroxy-heptyl)-α-xylohexp-(1→3)-β-L-Xylp.
structure, 2D NMR spectroscopy, lipooligosaccharide (LOS), Mycobacterium gastri LOS epitope, ELISA
NCBI PubMed ID: 7496145Journal NLM ID: 8603310Publisher: Kluwer Academic Publishers
Institutions: Laboratoire de Pharmacologie et de Toxicologie Fondamentales du Centre National de la Recherche Scientifique, Toulouse, France
Methods: NMR-2D, FAB-MS, GC-MS, NMR, HPLC, EI-MS
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5. Compound ID: 2073
|
a-L-Rhap2Me3Me4Me-(1-3)-+
|
-2)-a-L-Rhap3Me4Me-(1-4)-a-D-Glcp2Me3Me6Me-(1-3)-b-L-Rhap2Me4Me-(1-4)-b-D-Glcp2Me3Me6Me-(1-4)-a-D-Glcp2Me6Me-(1-
Me = -CD3 |
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Structure type: polymer chemical repeating unit
Compound class: EPS
Contained glycoepitopes: IEDB_128164,IEDB_136098,IEDB_136105,IEDB_137476,IEDB_137477,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_225177,IEDB_885823,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 678
Harding LP, Marshall VM, Elvin M, Gu Y, Laws AP "Structural characterisation of a perdeuteriomethylated exopolysaccharide by NMR spectroscopy: characterisation of the novel exopolysaccharide produced by Lactobacillus delbrueckii subsp. bulgaricus EU23" -
Carbohydrate Research 338(1) (2003) 61-67
The exopolysaccharide (EPS) from Lactobacillus delbrueckii subsp. bulgaricus EU23 was perdeuteriomethylated and the perdeuteriomethylated EPS (pdm-EPS) purified by elution from a C(18) Sep-Pak cartridge. Both 1D and 2D NMR spectra were recorded for the pdm-EPS and these were interpreted to provide assignments for the individual 1H and 13C resonances of the sugar residues of the repeating unit. [-2)aLRhap(1-4)aDGlcp(1-3)bLRha?(1-4)bDGlcp(1-4)[aLRha?(1-3)]aDGlcp(1-] Using a combination of the results from monomer analysis and linkage analysis of the native EPS and the ROESY and HMBC NMR spectra of the pdm-EPS the following structure has been determined for the repeating unit:A process for characterising polysaccharides having low solubility in aqueous solution is reported
structure, NMR spectroscopy, exopolysaccharide, 2D NMR, Lactobacillus delbrueckii
NCBI PubMed ID: 12504382Publication DOI: 10.1016/S0008-6215(02)00354-3Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: a.p.laws@hud.ac.uk
Institutions: School of Applied Sciences, University of Huddersfield, Queensgate, HD1 3DH, Huddersfield, UK
Methods: NMR-2D, NMR, sugar analysis, GPC, perdeuteriomethylation
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6. Compound ID: 2129
|
b-L-Xylp-(1-4)-b-L-Xylp-(1-4)-a-L-Rhap3Me-(1-3)-b-D-Galp-(1-3)-b-D-Glcp-(1-4)-a-D-Glcp-(1-1)-a-D-Glcp |
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Structure type: oligomer
Compound class: LOS
Contained glycoepitopes: IEDB_136044,IEDB_136105,IEDB_137472,IEDB_137477,IEDB_141794,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_190606,IEDB_225177,IEDB_742521,IEDB_885823,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 648
Gilleron M, Puzo G "Lipooligosaccharidic antigens from Mycobacterium kansasii and Mycobacterium gastri" -
Glycoconjugate Journal 12 (1995) 298-308
A set of Lipooligosaccharides (LOSs) has previously been characterized in M. gastri W471. The structure of the highly antigenic LOS (LOS-III) was elucidated and this molecule can unambiguously distinguish M. gastri from the opportunistic pathogen M. kansasii. In the present study, the structures of three other M. gastri W471 LOSs were determined by one-dimensional 1H NMR spectroscopy and gas liquid chromatography. They differ by the number of Xylp units and by the structure of the distal monosaccharide. The two dimensional (2D) NMR approach was successfully applied to the LOS antigen of M. kansasii to locate the acetyl and acyl substituents and to determine the anomeric configuration of the α-D-Fucp unit. The molecular specificity of anti-LOS-III antibodies was investigated and the LOS-III epitope was defined as the distal disaccharide: 3,6-dideoxy-4-C-(1,3-dimethoxy-4,5,6,7-tetrahydroxy-heptyl)-α-xylohexp-(1→3)-β-L-Xylp.
structure, 2D NMR spectroscopy, lipooligosaccharide (LOS), Mycobacterium gastri LOS epitope, ELISA
NCBI PubMed ID: 7496145Journal NLM ID: 8603310Publisher: Kluwer Academic Publishers
Institutions: Laboratoire de Pharmacologie et de Toxicologie Fondamentales du Centre National de la Recherche Scientifique, Toulouse, France
Methods: NMR-2D, FAB-MS, GC-MS, NMR, HPLC, EI-MS
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7. Compound ID: 2130
|
a-Sugp-(1-3)-b-L-Xylp-(1-4)-b-L-Xylp-(1-4)-b-L-Xylp-(1-4)-b-L-Xylp-(1-4)-b-L-Xylp-(1-4)-b-L-Xylp-(1-4)-b-L-Xylp-(1-4)-a-L-Rhap3Me-(1-3)-b-D-Galp-(1-3)-b-D-Glcp-(1-4)-a-D-Glcp-(1-1)-a-D-Glcp
Sug = 3,6-dideoxy-4-C-(1,3-dimethoxy-4,5,6,7-tetrahydroxy-heptyl)-α-xylohexopyranose = SMILES O{1}[C@@H]1[C@H](O)C[C@](O)(C(OC)CC(OC)C(O)C(O)C(O)CO)[C@@H](C)O1 |
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Structure type: oligomer
Compound class: LOS
Contained glycoepitopes: IEDB_136044,IEDB_136105,IEDB_137472,IEDB_137477,IEDB_141794,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_190606,IEDB_225177,IEDB_742521,IEDB_885823,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 648
Gilleron M, Puzo G "Lipooligosaccharidic antigens from Mycobacterium kansasii and Mycobacterium gastri" -
Glycoconjugate Journal 12 (1995) 298-308
A set of Lipooligosaccharides (LOSs) has previously been characterized in M. gastri W471. The structure of the highly antigenic LOS (LOS-III) was elucidated and this molecule can unambiguously distinguish M. gastri from the opportunistic pathogen M. kansasii. In the present study, the structures of three other M. gastri W471 LOSs were determined by one-dimensional 1H NMR spectroscopy and gas liquid chromatography. They differ by the number of Xylp units and by the structure of the distal monosaccharide. The two dimensional (2D) NMR approach was successfully applied to the LOS antigen of M. kansasii to locate the acetyl and acyl substituents and to determine the anomeric configuration of the α-D-Fucp unit. The molecular specificity of anti-LOS-III antibodies was investigated and the LOS-III epitope was defined as the distal disaccharide: 3,6-dideoxy-4-C-(1,3-dimethoxy-4,5,6,7-tetrahydroxy-heptyl)-α-xylohexp-(1→3)-β-L-Xylp.
structure, 2D NMR spectroscopy, lipooligosaccharide (LOS), Mycobacterium gastri LOS epitope, ELISA
NCBI PubMed ID: 7496145Journal NLM ID: 8603310Publisher: Kluwer Academic Publishers
Institutions: Laboratoire de Pharmacologie et de Toxicologie Fondamentales du Centre National de la Recherche Scientifique, Toulouse, France
Methods: NMR-2D, FAB-MS, GC-MS, NMR, HPLC, EI-MS
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8. Compound ID: 3816
|
a-L-Rhap3Me4Me-(1-1)-+
|
LIP-(1-2)-D-Phe-(1-2)-+ |
| |
a-L-Fucp-(1-3)-a-D-Glcp6Me-(1-3)-a-L-Rhap4Me-(1-3)-a-L-Rhap-(1-2)-a-L-6dTalp3Me-(1-3)-D-aThr-(1-2)-D-Ala-(1-2)-Subst
Subst = L-alaninol = SMILES N{2}[C@@H](C){1}CO |
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Structure type: oligomer
Trivial name: pGPL-I
Compound class: glycopeptidolipid (GPL)
Contained glycoepitopes: IEDB_136045,IEDB_136098,IEDB_136105,IEDB_137476,IEDB_137477,IEDB_142488,IEDB_142489,IEDB_144562,IEDB_144998,IEDB_146664,IEDB_152214,IEDB_158539,IEDB_174333,IEDB_225177,IEDB_885823,IEDB_983931,SB_192,SB_86
The structure is contained in the following publication(s):
- Article ID: 1450
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: 11814054Publication DOI: 10.1007/PL00000834Journal NLM ID: 9705402Publisher: 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)
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9. Compound ID: 3817
|
a-L-Rhap3Me4Me-(1-1)-+
|
LIP-(1-2)-D-Phe-(1-2)-+ |
| |
b-D-GlcpA2Me4Me-(1-4)-a-L-Fucp3Me-(1-3)-b-D-Glcp6Me-(1-3)-a-L-Rhap4Me-(1-3)-a-L-Rhap-(1-2)-a-L-6dTalp3Me-(1-3)-D-aThr-(1-2)-D-Ala-(1-2)-Subst
Subst = L-alaninol = SMILES N{2}[C@@H](C){1}CO |
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Structure type: oligomer
Trivial name: pGPL-II
Compound class: glycopeptidolipid (GPL)
Contained glycoepitopes: IEDB_115136,IEDB_136045,IEDB_136098,IEDB_136105,IEDB_137476,IEDB_137477,IEDB_140630,IEDB_142488,IEDB_142489,IEDB_144562,IEDB_146664,IEDB_152214,IEDB_174333,IEDB_225177,IEDB_423153,IEDB_885823,IEDB_983931,SB_192,SB_86
The structure is contained in the following publication(s):
- Article ID: 1450
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: 11814054Publication DOI: 10.1007/PL00000834Journal NLM ID: 9705402Publisher: 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)
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10. Compound ID: 3818
|
a-L-Rhap3Me4Me-(1-1)-+
|
LIP-(1-2)-D-Phe-(1-2)-+ |
| |
b-D-GlcpA4Me-(1-4)-a-L-Fucp3Me-(1-3)-b-D-Glcp6Me-(1-3)-a-L-Rhap4Me-(1-3)-a-L-Rhap-(1-2)-a-L-6dTalp3Me-(1-3)-D-aThr-(1-2)-D-Ala-(1-2)-Subst
Subst = L-alaninol = SMILES N{2}[C@@H](C){1}CO |
Show graphically |
Structure type: oligomer
Trivial name: pGPL-III
Compound class: glycopeptidolipid (GPL)
Contained glycoepitopes: IEDB_115136,IEDB_136045,IEDB_136098,IEDB_136105,IEDB_137476,IEDB_137477,IEDB_140630,IEDB_142488,IEDB_142489,IEDB_144562,IEDB_146664,IEDB_152214,IEDB_174333,IEDB_225177,IEDB_423153,IEDB_885823,IEDB_983931,SB_192,SB_86
The structure is contained in the following publication(s):
- Article ID: 1450
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: 11814054Publication DOI: 10.1007/PL00000834Journal NLM ID: 9705402Publisher: 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)
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11. Compound ID: 3819
|
a-L-Rhap3Me4Me-(1-2)-a-L-Rhap3Me4Me-(1-1)-+
|
a-L-Rhap3Me-(1-3)-+ |
| |
LIP-(1-2)-D-Phe-(1-2)-D-aThr-(1-2)-D-Ala-(1-2)-Subst
Subst = L-alaninol = SMILES N{2}[C@@H](C){1}CO |
Show graphically |
Structure type: oligomer
Trivial name: GPL-I
Compound class: glycopeptidolipid (GPL)
Contained glycoepitopes: IEDB_133754,IEDB_136098,IEDB_136105,IEDB_137476,IEDB_137477,IEDB_225177,IEDB_885823
The structure is contained in the following publication(s):
- Article ID: 1450
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: 11814054Publication DOI: 10.1007/PL00000834Journal NLM ID: 9705402Publisher: 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)
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12. Compound ID: 3820
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a-L-Rhap3Me-(1-2)-a-L-Rhap3Me4Me-(1-1)-+
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a-L-Rhap3Me-(1-3)-+ |
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LIP-(1-2)-D-Phe-(1-2)-D-aThr-(1-2)-D-Ala-(1-2)-Subst
Subst = L-alaninol = SMILES N{2}[C@@H](C){1}CO |
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Structure type: oligomer
Trivial name: GPL-II
Compound class: glycopeptidolipid (GPL)
Contained glycoepitopes: IEDB_133754,IEDB_136098,IEDB_136105,IEDB_137476,IEDB_137477,IEDB_225177,IEDB_885823
The structure is contained in the following publication(s):
- Article ID: 1450
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: 11814054Publication DOI: 10.1007/PL00000834Journal NLM ID: 9705402Publisher: 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)
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13. Compound ID: 3821
|
a-L-Rhap-(1-2)-a-L-Rhap3Me4Me-(1-1)-+
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a-L-Rhap3Me-(1-3)-+ |
| |
LIP-(1-2)-D-Phe-(1-2)-D-aThr-(1-2)-D-Ala-(1-2)-Subst
Subst = L-alaninol = SMILES N{2}[C@@H](C){1}CO |
Show graphically |
Structure type: oligomer
Trivial name: GPL-III
Compound class: glycopeptidolipid (GPL)
Contained glycoepitopes: IEDB_133754,IEDB_136098,IEDB_136105,IEDB_137476,IEDB_137477,IEDB_225177,IEDB_885823
The structure is contained in the following publication(s):
- Article ID: 1450
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: 11814054Publication DOI: 10.1007/PL00000834Journal NLM ID: 9705402Publisher: 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)
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14. Compound ID: 3822
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S-2)-a-L-Rhap3Me4Me-(1-1)-+
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a-L-Rhap3Me-(1-3)-+ |
| |
LIP-(1-2)-D-Phe-(1-2)-D-aThr-(1-2)-D-Ala-(1-2)-Subst
Subst = L-alaninol = SMILES N{2}[C@@H](C){1}CO |
Show graphically |
Structure type: oligomer
Trivial name: GPL-IV
Compound class: glycopeptidolipid (GPL)
Contained glycoepitopes: IEDB_136098,IEDB_136105,IEDB_137476,IEDB_137477,IEDB_137478,IEDB_225177,IEDB_885823
The structure is contained in the following publication(s):
- Article ID: 1450
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: 11814054Publication DOI: 10.1007/PL00000834Journal NLM ID: 9705402Publisher: 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)
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15. Compound ID: 3827
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LIP-(1-2)-+
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a-L-6dTalp3Me-(1-3)-L-Ser-(1-2)-L-Ser3(%)Me-(1-2)-L-Phe-(1-2)-+
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Lau-(1-2)-+ Lau-(1-2)-+ |
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a-L-Rhap2Me3Me4Me-(1-3)-a-L-Rhap-(1-3)-a-L-Rhap-(1-3)-a-L-Quip4Ac-(1-3)-D-aThr1Me |
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Structure type: oligomer
Trivial name: GPL-X-I
Compound class: glycopeptidolipid (GPL)
Contained glycoepitopes: IEDB_136098,IEDB_136105,IEDB_137476,IEDB_137477,IEDB_150900,IEDB_225177,IEDB_534864,IEDB_885823
The structure is contained in the following publication(s):
- Article ID: 1450
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: 11814054Publication DOI: 10.1007/PL00000834Journal NLM ID: 9705402Publisher: 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)
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