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Title: (Z)-Oxopropene-1,3-diyl, a linker for the conjugation of the thiol group of cysteine with amino-derivatized drugs
Author: Petit, Elena
Bosch Hereu, Lluís
Costa i Arnau, Anna M.
Vilarrasa i Llorens, Jaume
Keywords: Tiols
Reaccions d'addició
Enllaços químics
Síntesi orgànica
Addition reactions
Chemical bonds
Organic synthesis
Issue Date: 14-Sep-2019
Publisher: American Chemical Society
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.
Note: Versió postprint del document publicat a:
It is part of: Journal of Organic Chemistry, 2019, vol. 84, num. 17, p. 11170-11176
Related resource:
ISSN: 0022-3263
Appears in Collections:Articles publicats en revistes (Química Inorgànica i Orgànica)

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