Selective Derivatization of N-Terminal Cysteines Using Cyclopentenediones

作者:Brun Omar; Agramunt Jordi; Raich Lluis; Rovira Carme; Pedroso Enrique; Grandas Anna
来源:Organic Letters, 2016, 18(19): 4836-4839.
DOI:10.1021/acs.orglett.6b02301

摘要

The outcome of the Michael-type reaction between thiols and 2,2-disubstituted cyclopentenediones varies depending on the thiol. Stable compounds with two fused rings were formed upon reaction with 1,2-aminothiols (such as N-terminal cysteines in peptides). Other thiols gave reversibly Michael-type adducts that were in equilibrium with the starting materials. This differential reactivity allows differently placed cysteines to be distinguished and has been exploited to prepare bioconjugates incorporating two or three different moieties.

  • 出版日期2016-10-7