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1. Compound ID: 948
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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 (GPL)
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: 289
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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2. Compound ID: 994
|
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 (GPL)
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: 289
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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3. Compound ID: 995
|
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 (GPL)
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: 289
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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4. Compound ID: 5929
Structure type: oligomer
Trivial name: hapten
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: 2636
McNeil M, Tsang AY, Brennan PJ "Structure and antigenicity of the specific oligosaccharide hapten from the glycopeptidolipid antigen of Mycobacterium avium serotype 4, the dominant mycobacterium isolated from patients with acquired immune deficiency syndrome" -
Journal of Biological Chemistry 262(6) (1987) 2630-2635
A large number of patients with acquired immune deficiency syndrome develop disseminated infections due to member serotypes of the Mycobacterium avium complex. Seroagglutination on 181 such isolates followed by enzyme-linked immunosorbent assay and thin layer chromatography of the type-specific glycopeptidolipid (GPL) antigens demonstrated that the majority of serotypes were M. avium serotype 4. The specific GPL of serotype 4 was isolated in both the native, acetylated, and the deacetylated forms and its oligosaccharide hapten released as the oligosaccharide alditol by reductive β-elimination. A comprehensive structural analytical approach developed for more complex carbohydrates was applied to the oligosaccharide alditol in order to reveal glycosyl and glycosyl-linkage composition, sequence arrangements, ring forms, and enantiomeric and anomeric configurations. The structure of the triglycosyl alditol was established as, 4-O-Me-L-Rhap-(α1→4)-2-O-Me-L-Fucp-(α1→3)-L-Rhap-(α1→2)-6-deoxytalitol, in which the nonreducing-end disaccharide unit is unique to serotype 4. The native GPL antigen is diacetylated, presumably at other than the terminal disaccharide, since the antigenicity of both the acetylated and deacetylated antigens are comparable. The structure of the epitope of the type-specific antigen of serotype 4 will serve as the basis for synthetic antigen probes and the target for the monoclonal antibodies required to trace the origins in the environment of the infectious agent and study the epidemiology of human infections.
NCBI PubMed ID: 2434488Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Institutions: Department of Microbiology, Colorado State University, Fort Collins, Colorado 80523
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