Total Synthesis of an Immunogenic Trehalose Phospholipid from Salmonella Typhi and Elucidation of Its Sn-Regiochemistry by Mass Spectrometry

Overview

Journal Org Lett

Publisher American Chemical Society

Specialties Biochemistry
Chemistry

Date 2019 Jun 29

PMID 31247773

Citations 5

Authors

Vivek K Mishra

Jeffrey Buter

Molly S Blevins

Martin D Witte

Ildiko van Rhijn

D Branch Moody

Jennifer S Brodbelt

Adriaan J Minnaard

Affiliations

Soon will be listed here.

Abstract

Diphosphatidyltrehalose (diPT) is an immunogenic glycolipid, recently isolated from Salmonella Typhi. Despite rigorous structure elucidation, the sn-position of the acyl chains on the glycerol backbone had not been unequivocally established. A stereoselective synthesis of diPT and its regioisomer is reported herein. Using a hybrid MS approach combining collisional dissociation and ultraviolet photodissociation mass spectrometry for analysis of the regioisomers and natural diPT, the regiochemistry of the acyl chains of this abundant immunostimulatory glycolipid was established.

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