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Issue 35, 2017
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Total synthesis and mass spectrometric analysis of a Mycobacterium tuberculosis phosphatidylglycerol featuring a two-step synthesis of (R)-tuberculostearic acid

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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

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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., 2017,15, 7422-7429
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    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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