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Volume 148, Issue 6

Location of functional groups in mycobacterial meromycolate chains; the recognition of new structural principles in mycolic acids Free

Abstract

Mycobacterial α-, methoxy- and keto-mycolic acid methyl esters were separated by argentation chromatography into mycolates with no double bond, with one double bond or with one double bond. Meromycolic acids were prepared from each methyl mycolate fraction by pyrolysis, followed by silver oxide oxidation, and analysed by high-energy collision-induced dissociation/fast atom bombardment MS to reveal the exact locations of the functional groups within the meromycolate chain. The locations of and double bonds, and cyclopropane rings, methoxy and keto groups, and methyl branches within the meromycolate chain were determined from their characteristic fragment ion profiles, and the structures of the meromycolic acids, including those with three functional groups extracted from H37Ra, BCG and , were established. Meromycolic acids with one double bond were structurally closely related to those with one cyclopropane ring, whereas the meromycolic acids with one cyclopropane ring were closely related to the corresponding meromycolic acids with one cyclopropane ring. A close relationship between methoxy- and keto-meromycolic acids was also implied. The relationship between the meromycolic acids with a double bond and the other meromycolic acids was not clearly revealed, and they did not appear to be immediate substrates for cyclopropanation.

  • Received:
  • Accepted:
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  • Published Online:
Keyword(s): CID mass spectrometry , CID, collision-induced dissociation , FAB, fast atom bombardment , MAC, Mycobacterium avium complex , meromycolic acids , mu, mass unit measured in m/z and spacing between functional groups
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2002-06-01
2024-04-19
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Location of functional groups in mycobacterial meromycolate chains; the recognition of new structural principles in mycolic acids
Microbiology 148, 1881 (2002); https://doi.org/10.1099/00221287-148-6-1881
/content/journal/micro/10.1099/00221287-148-6-1881
/content/journal/micro/10.1099/00221287-148-6-1881
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