Show legend Show as text

Structure type: monomer
Aglycon: phenolphthiocerol dimycocerosate
Trivial name: phenolic mycoside
Compound class: glycolipid
Contained glycoepitopes: IEDB_136105,IEDB_137477,IEDB_225177,IEDB_885823

• Article ID: 1796
  Hartmann S, Minnikin DE, Mallet AI, Ridell M, Rigouts L, Portaels F "Fast atom bombardment mass spectrometry of mycobacterial phenolic glycolipids" - Biological Mass Spectrometry 23 (1994) 362-368
  

  Fast atom bombardment mass spectra were successfully recorded for intact glycosylphenolphthiocerol dimycocerosates (phenolic glycolipids, PGLs) from Mycobacterium kansasii, M. leprae, M. tuberculosis, M. marinum, M. bovis and M. haemophilum. Characteristic fragment ions from the loss of the oligosaccharide moiety and one of the long-chain multimethyl-branched mycocerosic acids were observed in most cases. A tandem mass spectrometric experiment was carried out on the PGL from M. tuberculosis, revealing the type of mycocerosic acids esterified to individual homologues. Mass spectra of homologues separated by reversed-phase high-performance liquid chromatography gave information on the substitution pattern in certain cases. The potential of matrix-assisted laser desorption ionization spectroscopy was demonstrated by a successful analysis of the PGL from M. tuberculosis.

  NCBI PubMed ID: 8038230
  Journal NLM ID: 9102982
  Institutions: Department of Chemistry, The University, Newcastle upon Tyne, UK
  Methods: FAB-MS
  
   
  
  Mycobacterium marinum
  CSDB ID 110029 (all data & tools)
• Article ID: 2703
  Daffé M, Varnerot A, Lévy-Frébault VV "The phenolic mycoside of Mycobacterium ulcerans: structure and taxonomic implications" - Journal of General Microbiology 138 (1992) 131-137
  

  Mycobacterium ulcerans and some pathogenic mycobacterial species elaborate wax A consisting of related long-chain beta-diol components (phthiocerol and related compounds) esterified by multimethyl-branched fatty acids. With the exception of M. ulcerans, wax A-containing mycobacteria also synthesize glycosylated phenol phthiocerol diester and related compounds: the so-called phenolic mycosides. In a deliberate effort to characterize this latter class of compounds in M. ulcerans, 20 strains were examined. Phenolic mycosides were found in two strains. Application of chemical analyses, including one- and two-dimensional NMR spectroscopy, allowed the structural elucidation of glycolipids identified as 3-O-methyl-α-L-rhamnosyl phenol phthiocerol diphthioceranate investigators. As phenolic mycosides are highly species-specific molecules, this finding stresses the close phylogenetic link between M. marinum and M. ulcerans. Incidentally, a survey of the mycolate content of M. ulcerans showed that methoxymycolate could not be detected in three strains.

  NCBI PubMed ID: 1556545
  Journal NLM ID: 0375371
  Institutions: Centre de Recherche de Biochimie et de Génétique Cellulaires du CNRS, Toulouse, France
  Methods: 1H NMR
  
   
  
  Mycobacterium ulcerans
  CSDB ID 139859 (all data & tools)