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

[Image: see text] 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...

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Autores principales: Mishra, Vivek K., Buter, Jeffrey, Blevins, Molly S., Witte, Martin D., Van Rhijn, Ildiko, Moody, D. Branch, Brodbelt, Jennifer S., Minnaard, Adriaan J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2019
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6614791/
https://www.ncbi.nlm.nih.gov/pubmed/31247773
http://dx.doi.org/10.1021/acs.orglett.9b01725
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author Mishra, Vivek K.
Buter, Jeffrey
Blevins, Molly S.
Witte, Martin D.
Van Rhijn, Ildiko
Moody, D. Branch
Brodbelt, Jennifer S.
Minnaard, Adriaan J.
author_facet Mishra, Vivek K.
Buter, Jeffrey
Blevins, Molly S.
Witte, Martin D.
Van Rhijn, Ildiko
Moody, D. Branch
Brodbelt, Jennifer S.
Minnaard, Adriaan J.
author_sort Mishra, Vivek K.
collection PubMed
description [Image: see text] 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(3) 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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spelling pubmed-66147912019-07-10 Total Synthesis of an Immunogenic Trehalose Phospholipid from Salmonella Typhi and Elucidation of Its sn-Regiochemistry by Mass Spectrometry Mishra, Vivek K. Buter, Jeffrey Blevins, Molly S. Witte, Martin D. Van Rhijn, Ildiko Moody, D. Branch Brodbelt, Jennifer S. Minnaard, Adriaan J. Org Lett [Image: see text] 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(3) 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. American Chemical Society 2019-06-20 2019-07-05 /pmc/articles/PMC6614791/ /pubmed/31247773 http://dx.doi.org/10.1021/acs.orglett.9b01725 Text en Copyright © 2019 American Chemical Society This is an open access article published under a Creative Commons Non-Commercial No Derivative Works (CC-BY-NC-ND) Attribution License (http://pubs.acs.org/page/policy/authorchoice_ccbyncnd_termsofuse.html) , which permits copying and redistribution of the article, and creation of adaptations, all for non-commercial purposes.
spellingShingle Mishra, Vivek K.
Buter, Jeffrey
Blevins, Molly S.
Witte, Martin D.
Van Rhijn, Ildiko
Moody, D. Branch
Brodbelt, Jennifer S.
Minnaard, Adriaan J.
Total Synthesis of an Immunogenic Trehalose Phospholipid from Salmonella Typhi and Elucidation of Its sn-Regiochemistry by Mass Spectrometry
title Total Synthesis of an Immunogenic Trehalose Phospholipid from Salmonella Typhi and Elucidation of Its sn-Regiochemistry by Mass Spectrometry
title_full Total Synthesis of an Immunogenic Trehalose Phospholipid from Salmonella Typhi and Elucidation of Its sn-Regiochemistry by Mass Spectrometry
title_fullStr Total Synthesis of an Immunogenic Trehalose Phospholipid from Salmonella Typhi and Elucidation of Its sn-Regiochemistry by Mass Spectrometry
title_full_unstemmed Total Synthesis of an Immunogenic Trehalose Phospholipid from Salmonella Typhi and Elucidation of Its sn-Regiochemistry by Mass Spectrometry
title_short Total Synthesis of an Immunogenic Trehalose Phospholipid from Salmonella Typhi and Elucidation of Its sn-Regiochemistry by Mass Spectrometry
title_sort total synthesis of an immunogenic trehalose phospholipid from salmonella typhi and elucidation of its sn-regiochemistry by mass spectrometry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6614791/
https://www.ncbi.nlm.nih.gov/pubmed/31247773
http://dx.doi.org/10.1021/acs.orglett.9b01725
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