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

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...

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Published inOrganic & biomolecular chemistry Vol. 15; no. 35; pp. 7422 - 7429
Main Authors Burugupalli, Satvika, Richardson, Mark B., Williams, Spencer J.
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 13.09.2017
Subjects
Chemistry
Chemistry, Organic
Mass Spectrometry
Molecular Structure
Mycobacterium tuberculosis - chemistry
Phosphatidylglycerols - analysis
Physical Sciences
Science & Technology
Stearic Acids - chemical synthesis
Stearic Acids - chemistry
Stereoisomerism
NKT CELLS
CARDIOLIPIN
DIPHOSPHATIDYLGLYCEROL
RECOGNITION
GLYCEROL
PHOSPHATIDYLINOSITOL
PHOSPHOLIPIDS
FATTY-ACIDS
MANNOSIDES
ELECTROSPRAY-IONIZATION
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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.
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ISSN:1477-0520
1477-0539
DOI:10.1039/c7ob01786c