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.
| 元の言語 | 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 |
| 発行部数 | 2 |
| DOI | |
| 出版物ステータス | Published - 2006 3 |
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ASJC Scopus subject areas
- Materials Science(all)
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An expeditious chemo-enzymatic synthesis of dihydronorcapsaicin β-d-glucopyranoside. / Sultana, Israt; Shimamoto, Miwa; Obata, Rika; Nishiyama, Shigeru; Sugai, Takeshi.
：: Science and Technology of Advanced Materials, 巻 7, 番号 2, 03.2006, p. 197-201.研究成果: Article
}
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 -