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
School of Pharmacy, Hyogo University of Health Sciences, Minatojima, Kobe 650-8530, Japan   eMail: miyabe@huhs.ac.jp
,
Yuya Goto
School of Pharmacy, Hyogo University of Health Sciences, Minatojima, Kobe 650-8530, Japan   eMail: miyabe@huhs.ac.jp
,
Ikko Minato
School of Pharmacy, Hyogo University of Health Sciences, Minatojima, Kobe 650-8530, Japan   eMail: miyabe@huhs.ac.jp
,
Hideto Miyabe*
School of Pharmacy, Hyogo University of Health Sciences, Minatojima, Kobe 650-8530, Japan   eMail: miyabe@huhs.ac.jp
› Institutsangaben
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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Publikationsverlauf

Received: 17. Mai 2017

Accepted after revision: 19. Juni 2017

Publikationsdatum:
25. Juli 2017 (online)


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.

Supporting Information