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1. Compound ID: 423
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Subst-(1-3)-b-D-Quip3N-(1-3)-a-L-Rhap4Me-(1-3)-a-L-Rhap-(1-3)-a-L-Rhap-(1-2)-a-L-6dTalp-(1--/p-trifluoroacetamidophenyl/
Subst = 3-hydroxy-2-methylbutanoic acid = SMILES CC(O)C(C){1}C(O)=O |
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Structure type: oligomer
Aglycon: p-trifluoroacetamidophenyl
Trivial name: pentasaccharide hapten
Contained glycoepitopes: IEDB_136098,IEDB_136105,IEDB_225177,IEDB_885823
The structure is contained in the following publication(s):
- Article ID: 154
Varga Z, Bajza I, Batta G, Lipták A "Synthesis of the pentasaccharide hapten from the glycopeptidolipid antigen of Mycobacterium avium serovar 17" -
Tetrahedron Letters 42(31) (2001) 5283-5286
Effective synthesis of the pentasaccharide hapten from the glycopeptidolipid antigen of Mycobacterium avium serovar 17 in a p-aminophenyl linker-containing form, using 3+2 block synthesis strategy, is described. A 2+3 block synthesis could not be achieved, although different glycosyl donors (1-Br, 1-SPh, 1-O-C(NH)CCl3) were used.
synthesis, antigen, oligosaccharide, Mycobacterium, block synthesis, glycopeptidolipid, hapten, linker, M.avium serovar 17, Mycobacteria, Mycobacterium avium, nilic acid, pentasaccharide
Journal NLM ID: 2984819RPublisher: Elsevier
Institutions: Department of Biochemistry, University of Debrecen, PO Box 55, Debrecen H- 4010, Hungary, Research Group for Carbohydrates of the Hungarian Academy of Sciences, PO Box 55, Debrecen H- 4010, Hungary, Research Group for Antibiotics of the Hungarian Academy of Sciences, PO Box 70, Debrecen H- 4010, Hungary
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2. Compound ID: 805
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a-L-Olip4Me-(1-3)-a-L-Fucp2Me4Pp-(1-3)-a-L-Rhap2Me-(1-3)-a-L-Rhap2Me4Me-(1--/phenolphthiocerol dimycocerostate/ |
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Structure type: oligomer
Aglycon: phenolphthiocerol dimycocerostate
Trivial name: phenolic glycolipid
Contained glycoepitopes: IEDB_136045,IEDB_136098,IEDB_136105,IEDB_142489,IEDB_144562,IEDB_152214,IEDB_174333,IEDB_225177,IEDB_885823,SB_86
The structure is contained in the following publication(s):
- Article ID: 215
Watanabe M, Aoyagi Y, Ohta A, Minnikin DE "Structures of phenolic glycolipids from Mycobacterium kansasii" -
European Journal of Biochemistry 248(1) (1997) 93-98
From the lipid fraction of cells of Mycobacterium kansasii, four phenolic glycolipids K5, K6, K7 and K8, were isolated, in addition to three known phenolic glycolipids KI, KII and KIV. K5 was identified as a tetraglycosyl phenolic glycolipid whose sugar moiety was 2,6-dideoxy-4-O-methyl-L-α-arabinohexopyranosyl(1→3)-4-O-pro pionyl-2-O-methyl-L-α-fucopyranosyl(1→3)-2-O-methyl-L-α-rhamno pyranosyl-(1→3)-2,4-di-O-methyl-L-α-rhamnopyranosyl(1→) and phenolic glycolipid K6 as deacetyl-KI. Glycolipids K7 and K8 were triglycosyl phenolic glycolipids having the sugar moieties of 2-O-methyl-L-α-fucopyranosyl(1→3)-2-O-methyl-L-α-rhamnopyranosyl(1→3)-2,4-di-O-methy-L-α-rhamnopyranosyl(1→) and 2-O-methyl-L-α-fucopyranosyl(1→3)-2-O-methyl-L-α-rhamnopyranosyl(1→3)-2-O-methyl-L-α-rhamnopyranosyl(1→), respectively. Phenolic glycolipids K6 and K7 have been referred to as controlled degradation products of phenolic glycolipid KI previously. Also isolated was 5-mycolyl-β-arabinofuranosyl(1→2)-5-mycolyl-α-arabinofurnosyl(1→1')-glycerol, an analogue of glycolipid ai, originally isolated from Mycobacterium avium-Mycobacterium intracellulare complex, having mycolic acids of M. kansasii.
structure, isolation, glycolipid ai, Mycobacterium kansasii, phenolic glycolipid
NCBI PubMed ID: 9310365Publication DOI: 10.1111/j.1432-1033.1997.00093.xJournal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: motokoko@triton.ps.toyaku.ac.jp
Institutions: School of Pharmacy, Tokyo University of Pharmacy and Life Science, Horinouchi, Hachioji, Tokyo, Japan, Department of Chemistry, University of Newcastle upon Tyne, Newcastle upon Tyne, UK
Methods: NMR-2D, NMR
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3. Compound ID: 806
|
a-L-Olip4Me-(1-3)-a-L-Fucp2Me4Ac-(1-3)-a-L-Rhap2Me-(1-3)-a-L-Rhap2Me4Me-(1--/phenolphthiocerol dimycocerostate/ |
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Structure type: oligomer
Aglycon: phenolphthiocerol dimycocerostate
Trivial name: phenolic glycolipid
Contained glycoepitopes: IEDB_136045,IEDB_136098,IEDB_136105,IEDB_142489,IEDB_144562,IEDB_152214,IEDB_174333,IEDB_225177,IEDB_885823,SB_86
The structure is contained in the following publication(s):
- Article ID: 215
Watanabe M, Aoyagi Y, Ohta A, Minnikin DE "Structures of phenolic glycolipids from Mycobacterium kansasii" -
European Journal of Biochemistry 248(1) (1997) 93-98
From the lipid fraction of cells of Mycobacterium kansasii, four phenolic glycolipids K5, K6, K7 and K8, were isolated, in addition to three known phenolic glycolipids KI, KII and KIV. K5 was identified as a tetraglycosyl phenolic glycolipid whose sugar moiety was 2,6-dideoxy-4-O-methyl-L-α-arabinohexopyranosyl(1→3)-4-O-pro pionyl-2-O-methyl-L-α-fucopyranosyl(1→3)-2-O-methyl-L-α-rhamno pyranosyl-(1→3)-2,4-di-O-methyl-L-α-rhamnopyranosyl(1→) and phenolic glycolipid K6 as deacetyl-KI. Glycolipids K7 and K8 were triglycosyl phenolic glycolipids having the sugar moieties of 2-O-methyl-L-α-fucopyranosyl(1→3)-2-O-methyl-L-α-rhamnopyranosyl(1→3)-2,4-di-O-methy-L-α-rhamnopyranosyl(1→) and 2-O-methyl-L-α-fucopyranosyl(1→3)-2-O-methyl-L-α-rhamnopyranosyl(1→3)-2-O-methyl-L-α-rhamnopyranosyl(1→), respectively. Phenolic glycolipids K6 and K7 have been referred to as controlled degradation products of phenolic glycolipid KI previously. Also isolated was 5-mycolyl-β-arabinofuranosyl(1→2)-5-mycolyl-α-arabinofurnosyl(1→1')-glycerol, an analogue of glycolipid ai, originally isolated from Mycobacterium avium-Mycobacterium intracellulare complex, having mycolic acids of M. kansasii.
structure, isolation, glycolipid ai, Mycobacterium kansasii, phenolic glycolipid
NCBI PubMed ID: 9310365Publication DOI: 10.1111/j.1432-1033.1997.00093.xJournal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: motokoko@triton.ps.toyaku.ac.jp
Institutions: School of Pharmacy, Tokyo University of Pharmacy and Life Science, Horinouchi, Hachioji, Tokyo, Japan, Department of Chemistry, University of Newcastle upon Tyne, Newcastle upon Tyne, UK
Methods: NMR-2D, NMR
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4. Compound ID: 807
|
a-L-Fucp2Me-(1-3)-a-L-Rhap2Me-(1-3)-a-L-Rhap2Me4Me-(1--/phenolphthiocerol dimycocerostate/ |
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Structure type: oligomer
Aglycon: phenolphthiocerol dimycocerostate
Trivial name: phenolic glycolipid
Contained glycoepitopes: IEDB_136045,IEDB_136098,IEDB_136105,IEDB_142489,IEDB_144562,IEDB_152214,IEDB_174333,IEDB_225177,IEDB_885823,SB_86
The structure is contained in the following publication(s):
- Article ID: 215
Watanabe M, Aoyagi Y, Ohta A, Minnikin DE "Structures of phenolic glycolipids from Mycobacterium kansasii" -
European Journal of Biochemistry 248(1) (1997) 93-98
From the lipid fraction of cells of Mycobacterium kansasii, four phenolic glycolipids K5, K6, K7 and K8, were isolated, in addition to three known phenolic glycolipids KI, KII and KIV. K5 was identified as a tetraglycosyl phenolic glycolipid whose sugar moiety was 2,6-dideoxy-4-O-methyl-L-α-arabinohexopyranosyl(1→3)-4-O-pro pionyl-2-O-methyl-L-α-fucopyranosyl(1→3)-2-O-methyl-L-α-rhamno pyranosyl-(1→3)-2,4-di-O-methyl-L-α-rhamnopyranosyl(1→) and phenolic glycolipid K6 as deacetyl-KI. Glycolipids K7 and K8 were triglycosyl phenolic glycolipids having the sugar moieties of 2-O-methyl-L-α-fucopyranosyl(1→3)-2-O-methyl-L-α-rhamnopyranosyl(1→3)-2,4-di-O-methy-L-α-rhamnopyranosyl(1→) and 2-O-methyl-L-α-fucopyranosyl(1→3)-2-O-methyl-L-α-rhamnopyranosyl(1→3)-2-O-methyl-L-α-rhamnopyranosyl(1→), respectively. Phenolic glycolipids K6 and K7 have been referred to as controlled degradation products of phenolic glycolipid KI previously. Also isolated was 5-mycolyl-β-arabinofuranosyl(1→2)-5-mycolyl-α-arabinofurnosyl(1→1')-glycerol, an analogue of glycolipid ai, originally isolated from Mycobacterium avium-Mycobacterium intracellulare complex, having mycolic acids of M. kansasii.
structure, isolation, glycolipid ai, Mycobacterium kansasii, phenolic glycolipid
NCBI PubMed ID: 9310365Publication DOI: 10.1111/j.1432-1033.1997.00093.xJournal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: motokoko@triton.ps.toyaku.ac.jp
Institutions: School of Pharmacy, Tokyo University of Pharmacy and Life Science, Horinouchi, Hachioji, Tokyo, Japan, Department of Chemistry, University of Newcastle upon Tyne, Newcastle upon Tyne, UK
Methods: NMR-2D, NMR
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5. Compound ID: 946
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a-L-Fucp-(1-3)-b-D-Glcp6Me-(1-3)-a-L-Rhap4Me-(1-3)-a-L-Rhap-(1-2)-6dTal3Me-ol |
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Structure type: oligomer
Compound class: glycopeptidolipid
Contained glycoepitopes: IEDB_136045,IEDB_136098,IEDB_136105,IEDB_142488,IEDB_142489,IEDB_144562,IEDB_146664,IEDB_152214,IEDB_174333,IEDB_225177,IEDB_885823,IEDB_983931,SB_192,SB_86
The structure is contained in the following publication(s):
- Article ID: 288
Khoo K, Chatterjee D, Dell A, Morris HR, Brennan PJ, Draper P "Novel O-methylated terminal glucuronyl characterizes the polar glycopeptidolipids of Mycobacterium habana strain TMC 5135" -
Journal of Biological Chemistry 271 (1996) 12333-12342
Mycobacterium "habana" strain TMC 5135, which has been proposed as a vaccine against both leprosy and tuberculosis, is considered to be a strain of serotype I of the recognized species Mycobacterium simiae. We have now shown that each of these strains possesses characteristic polar glycopeptidolipids (GPL) which are sufficiently different to allow unequivocal strain identification. Thin layer chromatographic analysis demonstrated that M. habana synthesizes a family of apolar GPLs and three distinct polar GPLs (pGPL-I to -III) which exhibited migration patterns different from those of M. simiae serotype I (pGPL-Sim). Using a combination of chemical, mass spectrometric, and proton-NMR analyses, the GPLs from M. habana were determined to be based on the same generic structure as those from the M. avium complex, namely N-fatty acyl-D-Phe-(O-saccharide)-D-allo-Thr-D-Ala-L-alaninyl-O-m onosaccharide. The de-O-acetylated apolar GPLs contain a 3-O-Me-6-deoxy-Tal attached to the allo-Thr and either a 3-O-Me-Rha or a 3,4-di-O-Me-Rha attached to the alaninol. In the pGPLs, oligosaccharides were found to be attached to the allo-Thr. The oligoglycosyl alditol reductively released from the least polar pGPL-I was fully characterized as L-Fucp α 1 in --7 with 3-(6-O-Me)-D-Glcp β 1 in --7 with 3-(4-O-Me)-L-Rhap α 1 in --7 with 3-L-Rhap α 1 in --7 with 2-(3-O-Me)-6-deoxy-Tal. In pGPl-II and -III, the terminal Fuc residue is further 3-O-methylated and 4-O-substituted with an additional 2,4-di-O-Me-D-GlcA and 4-O-Me-D-GlcA, respectively. The corresponding oligosaccharide from pGPL-Sim was shown to be of identical molecular weight to pGPL-II but terminating with a 3,4-di-O-Me-GlcA. Enzyme-linked immunosorbent assay-based serological studies using anti-M. habana and anti-M. simiae sera against whole cells and purified pGPLs firmly established the polar GPLs as important antigens and indicated that the terminal epitopes L-Fuc-, 2,4-di-O-Me-D-GlcA, and 4-O-Me-D-GlcA uniquely present in pGPL-I, -II, and -III, respectively, confer sufficient specificity for the identification of M. habana as a distinct serotype of M. simiae.
strain, terminal, acid, Mycobacterium, glycopeptidolipid, Mycobacteria, polar, glucuronyl
NCBI PubMed ID: 8647835Publication DOI: 10.1074/jbc.271.21.12333Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Correspondence: p-draper@nimr.mrc.ac.uk
Institutions: Department of Microbiology, Colorado State University, Fort Collins, Colorado 80523 and the Department of Biochemistry, Imperial College, London SW7 2AY and National Institute for Medical Research, The Ridgeway, Mill Hill, London NW71AA, United Kingdom.
Methods: 1H NMR, FAB-MS, TLC, serological methods, reductive elimination
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6. Compound ID: 992
|
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)-6dTal3Me-ol |
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Structure type: oligomer
Compound class: glycopeptidolipid
Contained glycoepitopes: IEDB_115136,IEDB_136045,IEDB_136098,IEDB_136105,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: 288
Khoo K, Chatterjee D, Dell A, Morris HR, Brennan PJ, Draper P "Novel O-methylated terminal glucuronyl characterizes the polar glycopeptidolipids of Mycobacterium habana strain TMC 5135" -
Journal of Biological Chemistry 271 (1996) 12333-12342
Mycobacterium "habana" strain TMC 5135, which has been proposed as a vaccine against both leprosy and tuberculosis, is considered to be a strain of serotype I of the recognized species Mycobacterium simiae. We have now shown that each of these strains possesses characteristic polar glycopeptidolipids (GPL) which are sufficiently different to allow unequivocal strain identification. Thin layer chromatographic analysis demonstrated that M. habana synthesizes a family of apolar GPLs and three distinct polar GPLs (pGPL-I to -III) which exhibited migration patterns different from those of M. simiae serotype I (pGPL-Sim). Using a combination of chemical, mass spectrometric, and proton-NMR analyses, the GPLs from M. habana were determined to be based on the same generic structure as those from the M. avium complex, namely N-fatty acyl-D-Phe-(O-saccharide)-D-allo-Thr-D-Ala-L-alaninyl-O-m onosaccharide. The de-O-acetylated apolar GPLs contain a 3-O-Me-6-deoxy-Tal attached to the allo-Thr and either a 3-O-Me-Rha or a 3,4-di-O-Me-Rha attached to the alaninol. In the pGPLs, oligosaccharides were found to be attached to the allo-Thr. The oligoglycosyl alditol reductively released from the least polar pGPL-I was fully characterized as L-Fucp α 1 in --7 with 3-(6-O-Me)-D-Glcp β 1 in --7 with 3-(4-O-Me)-L-Rhap α 1 in --7 with 3-L-Rhap α 1 in --7 with 2-(3-O-Me)-6-deoxy-Tal. In pGPl-II and -III, the terminal Fuc residue is further 3-O-methylated and 4-O-substituted with an additional 2,4-di-O-Me-D-GlcA and 4-O-Me-D-GlcA, respectively. The corresponding oligosaccharide from pGPL-Sim was shown to be of identical molecular weight to pGPL-II but terminating with a 3,4-di-O-Me-GlcA. Enzyme-linked immunosorbent assay-based serological studies using anti-M. habana and anti-M. simiae sera against whole cells and purified pGPLs firmly established the polar GPLs as important antigens and indicated that the terminal epitopes L-Fuc-, 2,4-di-O-Me-D-GlcA, and 4-O-Me-D-GlcA uniquely present in pGPL-I, -II, and -III, respectively, confer sufficient specificity for the identification of M. habana as a distinct serotype of M. simiae.
strain, terminal, acid, Mycobacterium, glycopeptidolipid, Mycobacteria, polar, glucuronyl
NCBI PubMed ID: 8647835Publication DOI: 10.1074/jbc.271.21.12333Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Correspondence: p-draper@nimr.mrc.ac.uk
Institutions: Department of Microbiology, Colorado State University, Fort Collins, Colorado 80523 and the Department of Biochemistry, Imperial College, London SW7 2AY and National Institute for Medical Research, The Ridgeway, Mill Hill, London NW71AA, United Kingdom.
Methods: 1H NMR, FAB-MS, TLC, serological methods, reductive elimination
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7. Compound ID: 993
|
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)-6dTal3Me-ol |
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Structure type: oligomer
Compound class: glycopeptidolipid
Contained glycoepitopes: IEDB_115136,IEDB_136045,IEDB_136098,IEDB_136105,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: 288
Khoo K, Chatterjee D, Dell A, Morris HR, Brennan PJ, Draper P "Novel O-methylated terminal glucuronyl characterizes the polar glycopeptidolipids of Mycobacterium habana strain TMC 5135" -
Journal of Biological Chemistry 271 (1996) 12333-12342
Mycobacterium "habana" strain TMC 5135, which has been proposed as a vaccine against both leprosy and tuberculosis, is considered to be a strain of serotype I of the recognized species Mycobacterium simiae. We have now shown that each of these strains possesses characteristic polar glycopeptidolipids (GPL) which are sufficiently different to allow unequivocal strain identification. Thin layer chromatographic analysis demonstrated that M. habana synthesizes a family of apolar GPLs and three distinct polar GPLs (pGPL-I to -III) which exhibited migration patterns different from those of M. simiae serotype I (pGPL-Sim). Using a combination of chemical, mass spectrometric, and proton-NMR analyses, the GPLs from M. habana were determined to be based on the same generic structure as those from the M. avium complex, namely N-fatty acyl-D-Phe-(O-saccharide)-D-allo-Thr-D-Ala-L-alaninyl-O-m onosaccharide. The de-O-acetylated apolar GPLs contain a 3-O-Me-6-deoxy-Tal attached to the allo-Thr and either a 3-O-Me-Rha or a 3,4-di-O-Me-Rha attached to the alaninol. In the pGPLs, oligosaccharides were found to be attached to the allo-Thr. The oligoglycosyl alditol reductively released from the least polar pGPL-I was fully characterized as L-Fucp α 1 in --7 with 3-(6-O-Me)-D-Glcp β 1 in --7 with 3-(4-O-Me)-L-Rhap α 1 in --7 with 3-L-Rhap α 1 in --7 with 2-(3-O-Me)-6-deoxy-Tal. In pGPl-II and -III, the terminal Fuc residue is further 3-O-methylated and 4-O-substituted with an additional 2,4-di-O-Me-D-GlcA and 4-O-Me-D-GlcA, respectively. The corresponding oligosaccharide from pGPL-Sim was shown to be of identical molecular weight to pGPL-II but terminating with a 3,4-di-O-Me-GlcA. Enzyme-linked immunosorbent assay-based serological studies using anti-M. habana and anti-M. simiae sera against whole cells and purified pGPLs firmly established the polar GPLs as important antigens and indicated that the terminal epitopes L-Fuc-, 2,4-di-O-Me-D-GlcA, and 4-O-Me-D-GlcA uniquely present in pGPL-I, -II, and -III, respectively, confer sufficient specificity for the identification of M. habana as a distinct serotype of M. simiae.
strain, terminal, acid, Mycobacterium, glycopeptidolipid, Mycobacteria, polar, glucuronyl
NCBI PubMed ID: 8647835Publication DOI: 10.1074/jbc.271.21.12333Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Correspondence: p-draper@nimr.mrc.ac.uk
Institutions: Department of Microbiology, Colorado State University, Fort Collins, Colorado 80523 and the Department of Biochemistry, Imperial College, London SW7 2AY and National Institute for Medical Research, The Ridgeway, Mill Hill, London NW71AA, United Kingdom.
Methods: 1H NMR, FAB-MS, TLC, serological methods, reductive elimination
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8. Compound ID: 2073
|
a-L-Rhap2Me3Me4Me-(1-3)-+
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-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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9. Compound ID: 3804
|
a-L-Rhap4Me-(1-4)-a-L-Fucp2Me-(1-3)-a-L-Rhap-(1-2)-a-L-6dTalp-(1-3)-D-aThr-(?--/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/ |
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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_136045,IEDB_136098,IEDB_136099,IEDB_136105,IEDB_142489,IEDB_144562,IEDB_152214,IEDB_174333,IEDB_225177,IEDB_885823,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: 3811
|
Lac-(1-4)-b-D-Quip4N3Me-(1-3)-a-L-Rhap4Me-(1-3)-a-L-Rhap-(1-3)-a-L-Rhap-(1-2)-a-L-6dTalp-(1-3)-D-aThr-(?--/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/ |
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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_136098,IEDB_136105,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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11. Compound ID: 3812
|
3HOBut-(1-3)-b-D-Quip3N2Me-(1-3)-a-L-Rhap4Me-(1-3)-a-L-Rhap-(1-3)-a-L-Rhap-(1-2)-a-L-6dTalp-(1-3)-D-aThr-(?--/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/ |
Show graphically |
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_136098,IEDB_136105,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: 3813
|
b-D-GlcpA3Me4Me-(1-3)-a-L-Rhap2Me4Me-(1-3)-a-L-Rhap3CMe-(1-3)-a-L-Rhap-(1-2)-a-L-6dTalp-(1-3)-D-aThr-(?--/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/ |
Show graphically |
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
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: 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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14. 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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15. 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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