Synthesis and structural characterization of three unique helicobacter pylori a-cholesteryl phosphatidyl glucosides

Huy Q. Nguyen, Ryan A. Davis, Jacquelyn Gervay-Hague

Research output: Contribution to journalArticlepeer-review

13 Scopus citations

Abstract

Steryl glycosides produced by bacteria play important biological roles in the evasion and modulation of host immunity. Step-economical syntheses of three cholesteryl-6-Ophosphatidyl-α-d-glucopyranosides (αCPG) unique to Helicobacter pylori have been achieved. The approach relies upon regioselective deprotection of per-O-trimethylsilyl-α-d-cholesterylglucoside at C6 followed by phosphoramidite coupling. Global TMS ether deprotection in the presence of oxygen and subsequent deprotection of the cyano ethyl phosphoester afforded the target compounds in 16-21% overall yield starting from d-glucose. The structures of these natural products were determined using a combination of 2D NMR methods and mass spectrometry. These robust synthesis and characterization protocols provide analogues to facilitate glycolipidomic profiling and biological studies.

Original languageEnglish (US)
Pages (from-to)13400-13403
Number of pages4
JournalAngewandte Chemie - International Edition
Volume53
Issue number49
DOIs
StatePublished - Dec 1 2014

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis

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