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

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

Research output: Contribution to journalArticle

7 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)197-201
Number of pages5
JournalScience and Technology of Advanced Materials
Volume7
Issue number2
DOIs
Publication statusPublished - 2006 Mar

Fingerprint

Nitriles
Lipases
Nutrition
Lipase
Hydroxyl Radical
Amines
vanillin

Keywords

  • Aminolysis
  • Capsaicin
  • Glucoside
  • Lipase
  • Vanillin

ASJC Scopus subject areas

  • Materials Science(all)

Cite this

An expeditious chemo-enzymatic synthesis of dihydronorcapsaicin β-d-glucopyranoside. / Sultana, Israt; Shimamoto, Miwa; Obata, Rika; Nishiyama, Shigeru; Sugai, Takeshi.

In: Science and Technology of Advanced Materials, Vol. 7, No. 2, 03.2006, p. 197-201.

Research output: Contribution to journalArticle

Sultana, Israt ; Shimamoto, Miwa ; Obata, Rika ; Nishiyama, Shigeru ; Sugai, Takeshi. / An expeditious chemo-enzymatic synthesis of dihydronorcapsaicin β-d-glucopyranoside. In: Science and Technology of Advanced Materials. 2006 ; Vol. 7, No. 2. pp. 197-201.
@article{ac96fe28855b4180baf0f048fecdd480,
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",
year = "2006",
month = "3",
doi = "10.1016/j.stam.2005.10.005",
language = "English",
volume = "7",
pages = "197--201",
journal = "Science and Technology of Advanced Materials",
issn = "1468-6996",
publisher = "IOP Publishing Ltd.",
number = "2",

}

TY - JOUR

T1 - An expeditious chemo-enzymatic synthesis of dihydronorcapsaicin β-d-glucopyranoside

AU - Sultana, Israt

AU - Shimamoto, Miwa

AU - Obata, Rika

AU - Nishiyama, Shigeru

AU - Sugai, Takeshi

PY - 2006/3

Y1 - 2006/3

N2 - 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.

AB - 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.

KW - Aminolysis

KW - Capsaicin

KW - Glucoside

KW - Lipase

KW - Vanillin

UR - http://www.scopus.com/inward/record.url?scp=33645875050&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=33645875050&partnerID=8YFLogxK

U2 - 10.1016/j.stam.2005.10.005

DO - 10.1016/j.stam.2005.10.005

M3 - Article

AN - SCOPUS:33645875050

VL - 7

SP - 197

EP - 201

JO - Science and Technology of Advanced Materials

JF - Science and Technology of Advanced Materials

SN - 1468-6996

IS - 2

ER -