An expeditious chemo-enzymatic synthesis of dihydronorcapsaicin β-d-glucopyranoside

Israt Sultana; Miwa Shimamoto; Rika Obata; Shigeru Nishiyama; Takeshi Sugai

doi:10.1016/j.stam.2005.10.005

An expeditious chemo-enzymatic synthesis of dihydronorcapsaicin β-d-glucopyranoside

Israt Sultana, Miwa Shimamoto, Rika Obata, Shigeru Nishiyama, Takeshi Sugai

研究成果: Article › 査読

8 被引用数 (Scopus)

抄録

A seven-step and scalable synthesis of dihydronorcapsaicin β-d-glucopyranoside, non-pungent and adrenal secretion enhancement activity (diet effect), was accomplished from vanillin. A simple and inexpensive glucosyl donor, acetobromoglucose, was reacted with phenolic hydroxyl group of α-iodovanillin nitrile under basic conditions. Another key step was the lipase-catalyzed coupling reaction of primary amine, which was resulted from the reduction of the glucosylated product, with methyl nonanoate.

本文言語	English
ページ（範囲）	197-201
ページ数	5
ジャーナル	Science and Technology of Advanced Materials
巻	7
号	2
DOI	https://doi.org/10.1016/j.stam.2005.10.005
出版ステータス	Published - 2006 3

ASJC Scopus subject areas

Materials Science(all)

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10.1016/j.stam.2005.10.005

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引用スタイル

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title = "An expeditious chemo-enzymatic synthesis of dihydronorcapsaicin β-d-glucopyranoside",

abstract = "A seven-step and scalable synthesis of dihydronorcapsaicin β-d-glucopyranoside, non-pungent and adrenal secretion enhancement activity (diet effect), was accomplished from vanillin. A simple and inexpensive glucosyl donor, acetobromoglucose, was reacted with phenolic hydroxyl group of α-iodovanillin nitrile under basic conditions. Another key step was the lipase-catalyzed coupling reaction of primary amine, which was resulted from the reduction of the glucosylated product, with methyl nonanoate.",

keywords = "Aminolysis, Capsaicin, Glucoside, Lipase, Vanillin",

author = "Israt Sultana and Miwa Shimamoto and Rika Obata and Shigeru Nishiyama and Takeshi Sugai",

note = "Funding Information: This work was accomplished as the 21st Century COE Program (KEIO LCC) from the Ministry of Education, Culture, Sports, Science, and Technology, Japan. Part of this work was also supported by Grant-in-Aid for Scientific Research (No. 16580092).",

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AU - Sultana, Israt

AU - Shimamoto, Miwa

AU - Obata, Rika

AU - Nishiyama, Shigeru

AU - Sugai, Takeshi

N1 - Funding Information: This work was accomplished as the 21st Century COE Program (KEIO LCC) from the Ministry of Education, Culture, Sports, Science, and Technology, Japan. Part of this work was also supported by Grant-in-Aid for Scientific Research (No. 16580092).

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KW - Aminolysis

KW - Capsaicin

KW - Glucoside

KW - Lipase

KW - Vanillin

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