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

doi:10.1016/j.tetlet.2017.06.034

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

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

3 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 language	English
Pages (from-to)	2915-2918
Number of pages	4
Journal	Tetrahedron Letters
Volume	58
Issue number	30
DOIs	https://doi.org/10.1016/j.tetlet.2017.06.034
Publication status	Published - 2017
Externally published	Yes

Keywords

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

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2017.06.034

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title = "Synthesis of polyunsaturated fatty acid-containing glucuronosyl-diacylglycerol through direct glycosylation",

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.",

keywords = "3,4-Dimethoxybenzyl group, Diacylglycerol, Glucuronosyldiacylglycerols, Glycosylation, Gold(I) catalysis",

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

note = "Funding Information: This work was partially supported by RIKEN project funding, JSPS KAKENHI Grant Numbers 16H01167 in Middle Molecular Strategy and 15K12760, and by the PRIME from Japan Agency for Medical Research and Development, AMED. Publisher Copyright: {\textcopyright} 2017 Elsevier Ltd",

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language = "English",

volume = "58",

pages = "2915--2918",

journal = "Tetrahedron Letters",

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T1 - Synthesis of polyunsaturated fatty acid-containing glucuronosyl-diacylglycerol through direct glycosylation

AU - Wang, Qianqian

AU - Kuramoto, Yuta

AU - Okazaki, Yozo

AU - Ota, Eisuke

AU - Morita, Masaki

AU - Hirai, Go

AU - Saito, Kazuki

AU - Sodeoka, Mikiko

N1 - Funding Information: This work was partially supported by RIKEN project funding, JSPS KAKENHI Grant Numbers 16H01167 in Middle Molecular Strategy and 15K12760, and by the PRIME from Japan Agency for Medical Research and Development, AMED. Publisher Copyright: © 2017 Elsevier Ltd

PY - 2017

Y1 - 2017

N2 - 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.

AB - 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.

KW - 3,4-Dimethoxybenzyl group

KW - Diacylglycerol

KW - Glucuronosyldiacylglycerols

KW - Glycosylation

KW - Gold(I) catalysis

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DO - 10.1016/j.tetlet.2017.06.034

M3 - Article

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SN - 0040-4039

VL - 58

SP - 2915

EP - 2918

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 30

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

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