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(Z)-Oxopropene-1,3-diyl, a linker for the conjugation of the thiol group of cysteine with amino-derivatized drugs Petit Roig, Elena Bosch Hereu, Lluís Costa i Arnau, Anna M. Vilarrasa i Llorens, Jaume Tiols Reaccions d'addició Enllaços químics Síntesi orgànica Thiols Addition reactions Chemical bonds Organic synthesis 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. 2020-04-02T09:54:36Z 2020-09-06T05:10:26Z 2019-09-14 2020-04-02T09:54:36Z info:eu-repo/semantics/article info:eu-repo/semantics/acceptedVersion Versió postprint del document publicat a: https://doi.org/10.1021/acs.joc.8b02686 Journal of Organic Chemistry, 2019, vol. 84, num. 17, p. 11170-11176 https://doi.org/10.1021/acs.joc.8b02686 (c) American Chemical Society , 2019 info:eu-repo/semantics/openAccess American Chemical Society Articles publicats en revistes (Química Inorgànica i Orgànica)