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Marin LML, Lanéelle MA, Promé D, Lanéelle G, Promé JC, Daffé M
Structure of a novel sulfate-containing mycobacterial glycolipid
Biochemistry 31(45) (1992)
11106-11111
|
S-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 = alaninol = SMILES N{2}C(C){1}CO |
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Mycobacterium fortuitum
(NCBI TaxID 1766,
species name lookup)
Taxonomic group: bacteria / Actinobacteria
(Phylum: Actinobacteria)
Associated disease: infection due to Mycobacterium fortuitum [ICD11:
XN8ZX 
]
The structure was elucidated in this paperNCBI PubMed ID: 1445849Journal NLM ID: 0370623Publisher: American Chemical Society
Institutions: Departement III, LPTF du CNRS, Toulouse, France
We described previously the unusual structures of the two major C-mycoside glycopeptidolipids from Mycobacterium fortuitum biovar. peregrinum. More polar glycolipids, potentially more interesting in terms of antigenicity, were also present in the strains. A combination of FAB mass spectrometry, NMR, chemical analyses, and radiolabeling was successfully applied to these glycolipids to arrive at the unexpected and novel structure for the more polar compound. This consisted of the "orthodox" basic structure of the apolar C-mycosides, modified at the alaninol end by the presence of a sulfate group on position 2 of a 3,4-di-O-methylrhamnosyl residue. This novel and second class of sulfate-containing mycobacterial glycolipid may provide a chemical basis for the differentiation and classification of members of the M. fortuitum complex, the main group causing human diseases among the many fast-growing mycobacteria widely distributed in nature.
Structure type: oligomer
Location inside paper: GPL III
Compound class: glycopeptidolipid
Contained glycoepitopes: IEDB_136098,IEDB_136105,IEDB_137476,IEDB_137477,IEDB_137478,IEDB_225177,IEDB_885823
Methods: 13C NMR, 1H NMR, IR, FAB-MS, TLC, FAB-MIKE
Comments, role: Parent molecule: C-mycoside
Related record ID(s): 107864
NCBI Taxonomy refs (TaxIDs): 1766Reference(s) to other database(s): GlycomeDB:
3298
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There is only one chemically distinct structure:
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Marin LML, Lanéelle MA, Promé D, Lanéelle G, Promé JC, Daffé M
Structure of a novel sulfate-containing mycobacterial glycolipid
Biochemistry 31(45) (1992)
11106-11111
|
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 = alaninol = SMILES N{2}C(C){1}CO |
Show graphically |
Mycobacterium fortuitum
(NCBI TaxID 1766,
species name lookup)
Taxonomic group: bacteria / Actinobacteria
(Phylum: Actinobacteria)
Associated disease: infection due to Mycobacterium fortuitum [ICD11:
XN8ZX ]
The structure was elucidated in this paperNCBI PubMed ID: 1445849Journal NLM ID: 0370623Publisher: American Chemical Society
Institutions: Departement III, LPTF du CNRS, Toulouse, France
We described previously the unusual structures of the two major C-mycoside glycopeptidolipids from Mycobacterium fortuitum biovar. peregrinum. More polar glycolipids, potentially more interesting in terms of antigenicity, were also present in the strains. A combination of FAB mass spectrometry, NMR, chemical analyses, and radiolabeling was successfully applied to these glycolipids to arrive at the unexpected and novel structure for the more polar compound. This consisted of the "orthodox" basic structure of the apolar C-mycosides, modified at the alaninol end by the presence of a sulfate group on position 2 of a 3,4-di-O-methylrhamnosyl residue. This novel and second class of sulfate-containing mycobacterial glycolipid may provide a chemical basis for the differentiation and classification of members of the M. fortuitum complex, the main group causing human diseases among the many fast-growing mycobacteria widely distributed in nature.
Structure type: oligomer
Location inside paper: GPL III
Compound class: glycopeptidolipid
Contained glycoepitopes: IEDB_133754,IEDB_136098,IEDB_136105,IEDB_137476,IEDB_137477,IEDB_225177,IEDB_885823
Methods: 13C NMR, 1H NMR, IR, FAB-MS, TLC, FAB-MIKE
Comments, role: Parent molecule: C-mycoside
Related record ID(s): 107863
NCBI Taxonomy refs (TaxIDs): 1766Reference(s) to other database(s): GlycomeDB:
4270
Show glycosyltransferases
There is only one chemically distinct structure:
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