Total Synthesis of an Immunogenic Trehalose Phospholipid from Salmonella Typhi and Elucidation of Its sn-Regiochemistry by Mass Spectrometry
Publication date
2019
Authors
Mishra, Vivek K.
Buter, Jeffrey
Blevins, Molly S.
Witte, Martin D.
Van Rhijn, Ildiko
Moody, D. Branch
Brodbelt, Jennifer S.
Minnaard, Adriaan J.
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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 MS3 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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Mishra, V K, Buter, J, Blevins, M S, Witte, M D, Van Rhijn, I, Moody, D B, Brodbelt, J S & Minnaard, A J 2019, 'Total Synthesis of an Immunogenic Trehalose Phospholipid from Salmonella Typhi and Elucidation of Its sn-Regiochemistry by Mass Spectrometry', Organic Letters, vol. 21, no. 13, pp. 5126-5131. https://doi.org/10.1021/acs.orglett.9b01725