Jump to main content
Jump to site search


Total synthesis and mass spectrometric analysis of a Mycobacterium tuberculosis phosphatidylglycerol featuring a two-step synthesis of (R)-tuberculostearic acid

Author affiliations

Abstract

We report the total synthesis of (R)-tuberculostearic acid-containing Mycobacterium tuberculosis phosphatidylglycerol (PG). The approach features a two-step synthesis of (R)-tuberculostearic acid, involving an (S)-citronellyl bromide linchpin, and the phosphoramidite-assisted assembly of the full PG structure. Collision-induced dissociation mass spectrometry of two chemically-synthesized PG acyl regioisomers revealed diagnostic product ions formed by preferential loss of carboxylate at the secondary (sn-2) position.

Graphical abstract: Total synthesis and mass spectrometric analysis of a Mycobacterium tuberculosis phosphatidylglycerol featuring a two-step synthesis of (R)-tuberculostearic acid

Back to tab navigation

Supplementary files

Publication details

The article was received on 20 Jul 2017, accepted on 11 Aug 2017 and first published on 11 Aug 2017


Article type: Paper
DOI: 10.1039/C7OB01786C
Citation: Org. Biomol. Chem., 2017, Advance Article
  •   Request permissions

    Total synthesis and mass spectrometric analysis of a Mycobacterium tuberculosis phosphatidylglycerol featuring a two-step synthesis of (R)-tuberculostearic acid

    S. Burugupalli, M. B. Richardson and S. J. Williams, Org. Biomol. Chem., 2017, Advance Article , DOI: 10.1039/C7OB01786C

Search articles by author

Spotlight

Advertisements