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2019-09-14

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Please use this identifier to cite or link to this item: https://hdl.handle.net/2445/154829

(Z)-Oxopropene-1,3-diyl, a linker for the conjugation of the thiol group of cysteine with amino-derivatized drugs

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https://doi.org/10.1021/acs.joc.8b02686

Abstract

We have developed a conjugation reaction based on the thia-Michael addition to activated triple bonds, which can be an alternative to maleimides, the most commonly used reagents to link thiol groups (of Cys) to drugs and labels. An amino group is converted into its propynamide and, in aqueous media at 37 °C and pH 7.4, Cys derivatives are added. The oxopropene-1,3-diyl linker is formed with excellent Z selectivity without secondary reactions. No exchange with other thiols is observed.

Subject

Tiols, Reaccions d'addició, Enllaços químics, Síntesi orgànica

Subject (English)

Thiols, Addition reactions, Chemical bonds, Organic synthesis

Citation

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Articles publicats en revistes (Química Inorgànica i Orgànica)

Citation

PETIT ROIG, Elena, et al. (Z)-Oxopropene-1,3-diyl, a linker for the conjugation of the thiol group of cysteine with amino-derivatized drugs. Journal of Organic Chemistry. 2019. Vol. 84, num. 17, pags. 11170-11176. ISSN 0022-3263. [consulted: 8 of August of 2026]. Available at: https://hdl.handle.net/2445/154829

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