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

8 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 1

Keywords

  • Aminolysis
  • Capsaicin
  • Glucoside
  • Lipase
  • Vanillin

ASJC Scopus subject areas

  • Materials Science(all)

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