A facile synthesis of isoflavone 7-O-glucuronides

Nawaf Al-Maharik, Nigel P. Botting

Research output: Contribution to journalArticlepeer-review

29 Citations (Scopus)

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 languageEnglish
Pages (from-to)8703-8706
Number of pages4
JournalTetrahedron Letters
Volume47
DOIs
Publication statusPublished - 4 Dec 2006

Keywords

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

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