Synthesis 2017; 49(21): 4887-4892
DOI: 10.1055/s-0036-1588497
paper
© Georg Thieme Verlag Stuttgart · New York

Aqueous-Medium Selective Modification of Cysteine and Related Thiols with Tricyclic Oxygen-Heterocycles

Eito Yoshioka, Yuya Goto, Ikko Minato, Hideto Miyabe*
  • School of Pharmacy, Hyogo University of Health Sciences, Minatojima, Kobe 650-8530, Japan   Email: miyabe@huhs.ac.jp
This work was partially supported by JSPS KAKENHI Grant-in-Aid for Scientific Research (C) Grant Number 15K07879 (to E.Y.).
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Publication History

Received: 17 May 2017

Accepted after revision: 19 June 2017

Publication Date:
25 July 2017 (eFirst)

Abstract

The utility of tricyclic oxygen-heterocycles as a reagent for the thiol-selective modification toward bioconjugation was demonstrated by the use of l-cysteine, homocysteine, captopril, and glutathione as a nucleophile having a thiol group. These trapping reactions proceeded under the mild and aqueous reaction conditions.

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