Issue 35, 2017

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

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

Supplementary files

Article information

Article type
Paper
Submitted
20 Jul 2017
Accepted
11 Aug 2017
First published
11 Aug 2017
This article is Open Access
Creative Commons BY license

Org. Biomol. Chem., 2017,15, 7422-7429

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, 15, 7422 DOI: 10.1039/C7OB01786C

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