A facile synthesis of isoflavone 7-O-glucuronides

Nawaf Al-Maharik; Nigel P. Botting

doi:10.1016/j.tetlet.2006.10.034

A facile synthesis of isoflavone 7-O-glucuronides

Nawaf Al-Maharik, Nigel P. Botting

Research output: Contribution to journal › Article › peer-review

Abstract

An efficient method is presented for the synthesis of isoflavone 7-glucuronides using a N-(4-methoxyphenyl)-trifluoroacetimidate glucuronsyl donor. A 4-hexanoyl derivative of the isoflavone is used in the coupling reaction, both for protection and to improve solubility. These glucuronides are the human metabolites of estrogenic dietary isotlavones, but their biological activity and pharmacokinetics have yet to be established as until now there were no good methods for their synthesis. (c) 2006 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	8703-8706
Number of pages	4
Journal	Tetrahedron Letters
Volume	47
DOIs	https://doi.org/10.1016/j.tetlet.2006.10.034
Publication status	Published - 4 Dec 2006

Keywords

isoflavones
glucuronides
phytoestrogens
glycosylation
PHYTO-ESTROGENS
SOY
DAIDZEIN
FOOD
PHYTOESTROGENS
METABOLISM
ABSORPTION
GENISTEIN
INFANTS
HUMANS

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10.1016/j.tetlet.2006.10.034

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title = "A facile synthesis of isoflavone 7-O-glucuronides",

abstract = "An efficient method is presented for the synthesis of isoflavone 7-glucuronides using a N-(4-methoxyphenyl)-trifluoroacetimidate glucuronsyl donor. A 4-hexanoyl derivative of the isoflavone is used in the coupling reaction, both for protection and to improve solubility. These glucuronides are the human metabolites of estrogenic dietary isotlavones, but their biological activity and pharmacokinetics have yet to be established as until now there were no good methods for their synthesis. (c) 2006 Elsevier Ltd. All rights reserved.",

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author = "Nawaf Al-Maharik and Botting, {Nigel P.}",

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doi = "10.1016/j.tetlet.2006.10.034",

language = "English",

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journal = "Tetrahedron Letters",

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T1 - A facile synthesis of isoflavone 7-O-glucuronides

AU - Al-Maharik, Nawaf

AU - Botting, Nigel P.

PY - 2006/12/4

Y1 - 2006/12/4

N2 - An efficient method is presented for the synthesis of isoflavone 7-glucuronides using a N-(4-methoxyphenyl)-trifluoroacetimidate glucuronsyl donor. A 4-hexanoyl derivative of the isoflavone is used in the coupling reaction, both for protection and to improve solubility. These glucuronides are the human metabolites of estrogenic dietary isotlavones, but their biological activity and pharmacokinetics have yet to be established as until now there were no good methods for their synthesis. (c) 2006 Elsevier Ltd. All rights reserved.

AB - An efficient method is presented for the synthesis of isoflavone 7-glucuronides using a N-(4-methoxyphenyl)-trifluoroacetimidate glucuronsyl donor. A 4-hexanoyl derivative of the isoflavone is used in the coupling reaction, both for protection and to improve solubility. These glucuronides are the human metabolites of estrogenic dietary isotlavones, but their biological activity and pharmacokinetics have yet to be established as until now there were no good methods for their synthesis. (c) 2006 Elsevier Ltd. All rights reserved.

KW - isoflavones

KW - glucuronides

KW - phytoestrogens

KW - glycosylation

KW - PHYTO-ESTROGENS

KW - SOY

KW - DAIDZEIN

KW - FOOD

KW - PHYTOESTROGENS

KW - METABOLISM

KW - ABSORPTION

KW - GENISTEIN

KW - INFANTS

KW - HUMANS

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U2 - 10.1016/j.tetlet.2006.10.034

DO - 10.1016/j.tetlet.2006.10.034

M3 - Article

SN - 0040-4039

VL - 47

SP - 8703

EP - 8706

JO - Tetrahedron Letters

JF - Tetrahedron Letters

ER -

A facile synthesis of isoflavone 7-O-glucuronides

Abstract

Keywords

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