( Z )-Oxopropene-1,3-diyl, a Linker for the Conjugation of the Thiol Group of Cysteine with Amino-Derivatized Drugs
2019; American Chemical Society; Volume: 84; Issue: 17 Linguagem: Inglês
10.1021/acs.joc.8b02686
ISSN1520-6904
AutoresElena Petit, Lluís Bosch, Anna M. Costa, Jaume Vilarrasa,
Tópico(s)Sulfur-Based Synthesis Techniques
ResumoWe 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.
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