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

Vivek Mishra; Jeffrey Buter; Molly Blevins; Martin Witte; Ildiko van Rhijn; Branch  Moody; Jennifer Brodbelt; Adriaan Minnaard

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

Vivek Mishra
, Jeffrey Buter
, Molly Blevins
, Martin Witte
, Ildiko van Rhijn
, Branch Moody
, Jennifer Brodbelt
, Adriaan Minnaard

Stratingh Institute, University of Groningen
University of Texas, Department of Chemistry
Brigham and Women's Hospital, Division of Rheumatology, Immunology and Allergy
Utrecht University, School of Veterinary Medicine, Department of Infectious Diseases and Immunology

Research output: Contribution to journal › Article › Academic › peer-review

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.

Original language	English
Pages (from-to)	5126–5131
Journal	Organic Letters
Volume	23
Issue number	13
Publication status	Published - 20 Jun 2019
Externally published	Yes

Keywords

organic chemistry
total synthesis
natural product
analytical chemistry
mass spectrometry

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https://doi.org/10.1021/acs.orglett.9b01725Licence: CC BY-NC-ND

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title = "Total Synthesis of an Immunogenic Trehalose Phospholipid from Salmonella Typhi and Elucidation of Its sn-Regiochemistry by Mass Spectrometry",

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.",

keywords = "organische chemie, totale synthese, natuurlijk product, analytische chemie, massaspectrometrie, organic chemistry, total synthesis, natural product, analytical chemistry, mass spectrometry",

author = "Vivek Mishra and Jeffrey Buter and Molly Blevins and Martin Witte and \{van Rhijn\}, Ildiko and Branch Moody and Jennifer Brodbelt and Adriaan Minnaard",

year = "2019",

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language = "English",

volume = "23",

pages = "5126–5131",

journal = "Organic Letters",

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TY - JOUR

T1 - Total Synthesis of an Immunogenic Trehalose Phospholipid from Salmonella Typhi and Elucidation of Its sn-Regiochemistry by Mass Spectrometry

AU - Mishra, Vivek

AU - Buter, Jeffrey

AU - Blevins, Molly

AU - Witte, Martin

AU - van Rhijn, Ildiko

AU - Moody, Branch

AU - Brodbelt, Jennifer

AU - Minnaard, Adriaan

PY - 2019/6/20

Y1 - 2019/6/20

N2 - 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.

AB - 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.

KW - organische chemie

KW - totale synthese

KW - natuurlijk product

KW - analytische chemie

KW - massaspectrometrie

KW - organic chemistry

KW - total synthesis

KW - natural product

KW - analytical chemistry

KW - mass spectrometry

M3 - Article

SN - 1523-7052

VL - 23

SP - 5126

EP - 5131

JO - Organic Letters

JF - Organic Letters

IS - 13

ER -

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

Abstract

Keywords

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