Total Synthesis of the Photorhabdus temperata ssp. Cinereal 3240 Zwitterionic Trisaccharide Repeating Unit

Zwitterionic carbohydrate modifications, such as phosphoethanolamine (PEtN), govern host-pathogen interactions. Whereas it is recognized that these modifications stimulate the host immune system, the purpose of PEtN modification remains largely descriptive. As an enabling step toward studying this carbohydrate modification, we report a synthesis of the P. temperata zwitterionic trisaccharide repeating unit. The 32-step synthesis was enabled by H-phosphonate chemistry to install the PEtN arm on a poorly reactive and sterically hindered C4-alcohol.

Medienart:

E-Artikel

Erscheinungsjahr:

2021

Erschienen:

2021

Enthalten in:

Zur Gesamtaufnahme - volume:23

Enthalten in:

Organic letters - 23(2021), 15 vom: 06. Aug., Seite 5922-5926

Sprache:

Englisch

Beteiligte Personen:

Nguyen, Johny M [VerfasserIn]
Townsend, Steven D [VerfasserIn]

Links:

Volltext

Themen:

78A2BX7AEU
Ethanolamines
Journal Article
Phosphorylethanolamine
Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't
Trisaccharides

Anmerkungen:

Date Completed 23.11.2021

Date Revised 07.02.2022

published: Print-Electronic

Citation Status MEDLINE

doi:

10.1021/acs.orglett.1c02023

funding:

Förderinstitution / Projekttitel:

PPN (Katalog-ID):

NLM32858892X