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Article

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Accepted version

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2016

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Please use this identifier to cite or link to this item: https://hdl.handle.net/2445/102811

Selective derivatization of N-terminal cysteines using cyclopentenediones

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http://dx.doi.org/10.1021/acs.orglett.6b02301

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.

Subject

Bioquímica, Reaccions químiques, Cisteïna

Subject (English)

Biochemistry, Chemical reactions, Cysteine

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Articles publicats en revistes (Química Inorgànica i Orgànica)

Citation

BRUN CUBERO, Omar, et al. Selective derivatization of N-terminal cysteines using cyclopentenediones. Organic Letters. 2016. Vol. 18, num. 19, pags. 4836-4839. ISSN 1523-7060. [consulted: 15 of August of 2026]. Available at: https://hdl.handle.net/2445/102811

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