An expeditious chemo-enzymatic synthesis of dihydronorcapsaicin β-D-glucopyranoside
Open Access
- 1 January 2006
- journal article
- Published by Taylor & Francis in Science and Technology of Advanced Materials
- Vol. 7 (2) , 197-201
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
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