Please use this identifier to cite or link to this item:
http://hdl.handle.net/2445/154829
Title: | (Z)-Oxopropene-1,3-diyl, a linker for the conjugation of the thiol group of cysteine with amino-derivatized drugs |
Author: | Petit Roig, Elena Bosch Hereu, Lluís Costa i Arnau, Anna M. Vilarrasa i Llorens, Jaume |
Keywords: | Tiols Reaccions d'addició Enllaços químics Síntesi orgànica Thiols 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: https://doi.org/10.1021/acs.joc.8b02686 |
It is part of: | Journal of Organic Chemistry, 2019, vol. 84, num. 17, p. 11170-11176 |
URI: | http://hdl.handle.net/2445/154829 |
Related resource: | https://doi.org/10.1021/acs.joc.8b02686 |
ISSN: | 0022-3263 |
Appears in Collections: | Articles publicats en revistes (Química Inorgànica i Orgànica) |
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