Total synthesis and mass spectrometric analysis of a Mycobacterium tuberculosis phosphatidylglycerol featuring a two-step synthesis of (R)-tuberculostearic acidElectronic supplementary information (ESI) available. See DOI: 10.1039/c7ob01786c

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 f...

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Bibliographic Details
Main Authors Burugupalli, Satvika, Richardson, Mark B, Williams, Spencer J
Format Journal Article
LanguageEnglish
Published 13.09.2017
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Summary: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. A two-step synthesis of ( R )-tuberculostearic acid enables the total synthesis of a Mycobacterium tuberculosis phosphatidylglycerol. Mass spectrometric fragmentation of synthetic PG regioisomers of acylation patterns.
Bibliography:10.1039/c7ob01786c
Electronic supplementary information (ESI) available. See DOI
ISSN:1477-0520
1477-0539
DOI:10.1039/c7ob01786c