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Title: Selective derivatization of N-terminal cysteines using cyclopentenediones
Author: Brun, Omar
Agramunt, Jordi
Raich, Lluís
Rovira i Virgili, Carme
Pedroso Muller, Enrique
Grandas Sagarra, Anna
Keywords: Bioquímica
Reaccions químiques
Chemical reactions
Issue Date: 2016
Publisher: American Chemical Society
Abstract: 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.
Note: Versió postprint del document publicat a:
It is part of: Organic Letters, 2016, vol. 18, num. 19, p. 4836-4839
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ISSN: 1523-7060
Appears in Collections:Articles publicats en revistes (Química Inorgànica i Orgànica)

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