Synthesis of polyunsaturated fatty acid-containing glucuronosyl-diacylglycerol through direct glycosylation

Qianqian Wang, Yuta Kuramoto, Yozo Okazaki, Eisuke Ota, Masaki Morita, Go Hirai, Kazuki Saito, Mikiko Sodeoka

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

We describe a total synthesis of a polyunsaturated fatty acid (PUFA)-containing glucuronosyldiacylglycerol (GlcADG), which is a surrogate glycolipid whose synthesis is remarkably upregulated in plant membranes under phosphorus-depleted conditions. Glycosylation between the glucuronide donor bearing 3,4-dimethoxybenzyl (DMPM) protecting groups and di-acylglycerol acceptor proceeded smoothly in the presence of gold(I) catalyst to provide the protected α-isomer of GlcADG as the major product.

Original languageEnglish
Pages (from-to)2915-2918
Number of pages4
JournalTetrahedron Letters
Volume58
Issue number30
DOIs
Publication statusPublished - 2017 Jan 1
Externally publishedYes

Keywords

  • 3,4-Dimethoxybenzyl group
  • Diacylglycerol
  • Glucuronosyldiacylglycerols
  • Glycosylation
  • Gold(I) catalysis

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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