Chemoenzymatic synthesis of cholesteryl-6-O-tetradecanoyl-α-d- glucopyranoside: A product of host cholesterol efflux promoted by Helicobacter pylori

Ryan A. Davis, Chun Hung Lin, Jacquelyn Gervay-Hague

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

In a three-step protocol involving regioselective enzymatic acylation, per-O-trimethylsilylation, and a one-pot α-glycosidation-deprotection sequence, cholesteryl-6-O-tetradecanoyl-α-d-glucopyranoside (α-CAG) of Helicobacter pylori is afforded starting from glucose in an overall yield of 45%. The production of CAG can be scaled to make purified quantities available to the biological community for the first time.

Original languageEnglish (US)
Pages (from-to)9083-9085
Number of pages3
JournalChemical Communications
Volume48
Issue number72
DOIs
StatePublished - Sep 18 2012

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Acylation
Cholesterol
Glucose
Biota

ASJC Scopus subject areas

  • Metals and Alloys
  • Materials Chemistry
  • Surfaces, Coatings and Films
  • Electronic, Optical and Magnetic Materials
  • Ceramics and Composites
  • Catalysis
  • Chemistry(all)

Cite this

Chemoenzymatic synthesis of cholesteryl-6-O-tetradecanoyl-α-d- glucopyranoside : A product of host cholesterol efflux promoted by Helicobacter pylori. / Davis, Ryan A.; Lin, Chun Hung; Gervay-Hague, Jacquelyn.

In: Chemical Communications, Vol. 48, No. 72, 18.09.2012, p. 9083-9085.

Research output: Contribution to journalArticle

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