An expeditious chemo-enzymatic synthesis of dihydronorcapsaicin β-D-glucopyranoside
An expeditious chemo-enzymatic synthesis of dihydronorcapsaicin β-D-glucopyranoside
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DOI：
10.1016/j.stam.2005.10.005
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发表时间：
2006-03-01
影响因子：
5.5
通讯作者：
Sugai, Takeshi
中科院分区：
文献类型：
--
作者：
Sultana, Israt;Shimamoto, Miwa;Sugai, Takeshi
从香草醛完成了具有非刺激性和肾上腺分泌增强活性（饮食效应）的二氢去甲辣椒素β-D-吡喃葡萄糖苷的七步可放大合成。在碱性条件下，用一种简单廉价的葡萄糖基供体乙酰溴葡萄糖与α-碘代香草醛腈的酚羟基反应。另一个关键步骤是脂肪酶催化的伯胺与壬酸甲酯的偶联反应，该反应是由葡萄糖基化产物的还原产生的。(c)2006年由Elsevier Ltd.出版
A seven-step and scalable synthesis of dihydronorcapsaicin beta-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 alpha-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. (c) 2006 Published by Elsevier Ltd.