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

Fingerprint

Glycosylation
Glycerides
Glycolipids
Glucuronides
Unsaturated Fatty Acids
Gold
Phosphorus
Bearings (structural)
Membranes
Isomers
Catalysts
glucuronosyl diacylglycerol

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Wang, Q., Kuramoto, Y., Okazaki, Y., Ota, E., Morita, M., Hirai, G., ... Sodeoka, M. (2017). Synthesis of polyunsaturated fatty acid-containing glucuronosyl-diacylglycerol through direct glycosylation. Tetrahedron Letters, 58(30), 2915-2918. https://doi.org/10.1016/j.tetlet.2017.06.034

Synthesis of polyunsaturated fatty acid-containing glucuronosyl-diacylglycerol through direct glycosylation. / Wang, Qianqian; Kuramoto, Yuta; Okazaki, Yozo; Ota, Eisuke; Morita, Masaki; Hirai, Go; Saito, Kazuki; Sodeoka, Mikiko.

In: Tetrahedron Letters, Vol. 58, No. 30, 01.01.2017, p. 2915-2918.

Research output: Contribution to journalArticle

Wang, Q, Kuramoto, Y, Okazaki, Y, Ota, E, Morita, M, Hirai, G, Saito, K & Sodeoka, M 2017, 'Synthesis of polyunsaturated fatty acid-containing glucuronosyl-diacylglycerol through direct glycosylation', Tetrahedron Letters, vol. 58, no. 30, pp. 2915-2918. https://doi.org/10.1016/j.tetlet.2017.06.034
Wang, Qianqian ; Kuramoto, Yuta ; Okazaki, Yozo ; Ota, Eisuke ; Morita, Masaki ; Hirai, Go ; Saito, Kazuki ; Sodeoka, Mikiko. / Synthesis of polyunsaturated fatty acid-containing glucuronosyl-diacylglycerol through direct glycosylation. In: Tetrahedron Letters. 2017 ; Vol. 58, No. 30. pp. 2915-2918.
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AU - Hirai, Go

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