Taxonomic group: bacteria / Actinobacteria
(Phylum: Actinobacteria)
Associated disease: infection due to Mycobacterium leprae [ICD11:
XN5TS 
];
infection due to Mycobacterium tuberculosis [ICD11:
XN1N2 ]
NCBI PubMed ID: 7772860Publication DOI: 10.1093/glycob/5.1.117Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Institutions: Department of Biochemistry, Imperial College, London, UK.
Based on chemical analysis, we have previously concluded that the biologically important lipoarabinomannan (LAM) and lipomannan (LM) from Mycobacterium are multiglycosylated forms of the phosphatidylinositol mannosides (PIMs), the characteristic cell envelope mannophosphoinositides of mycobacteria. Using definitive analytical techniques, we have now re-examined the reported multiacylated nature of PIMs in order to gain a better insight into their possible roles as biosynthetic precursors of LM and LAM. High-sensitivity fast atom bombardment-mass spectrometry analyses of the perdeuteroacetyl and permethyl derivatives of PIMs from Mycobacterium tuberculosis and Mycobacterium leprae enabled us to define the exact fatty acyl compositions of the multiacylated, heterogeneous PIM families, notably the dimannoside (PIM2) and the hexamannoside (PIM6). Specifically, in conjunction with other chemical and gas chromatography-mass spectrometry (GC-MS) analyses, the additional C16 fatty acyl substituent on PIM2 and its lyso form were defined as attached to the C6 position of mannose. We also present evidence for triacylated mannophosphoinositide as a common lipid anchor for both LM and LAM, and further postulate that acylation of PIM2 may constitute a key regulatory step in their biosynthesis.
lipoarabinomannan, Mycobacterium tuberculosis, lipomannan, phosphatidylinositol mannosides, FAB-MS
Structure type: oligomer
Location inside paper: LM
Aglycon: phosphatidylinositol, PI
Trivial name: mannophosphoinositide, phosphatidylinositol mannoside, PIM
Compound class: lipomannan
Contained glycoepitopes: IEDB_130701,IEDB_144983,IEDB_144993,IEDB_152206,IEDB_983930,SB_44,SB_67,SB_72
Related record ID(s): 127448, 127450, 127451, 127452, 127453, 127454, 227454
NCBI Taxonomy refs (TaxIDs): 1769,
1773
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There is only one chemically distinct structure:
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