Selective Derivatization of N-Terminal Cysteines Using Cyclopentenediones.
The outcome of the Michael-type reaction between thiols and 2,2-disubstituted cyclopentenediones varies depending on the thiol. Stable compounds with two fused rings were formed upon reaction with 1,2-aminothiols (such as N-terminal cysteines in peptides). Other thiols gave reversibly Michael-type adducts that were in equilibrium with the starting materials. This differential reactivity allows differently placed cysteines to be distinguished and has been exploited to prepare bioconjugates incorporating two or three different moieties.
Omar
O
Brun
Jordi
J
Agramunt
Lluis
L
Raich
Institució Catalana de Recerca i Estudis Avançats (ICREA) , Passeig Lluis Companys 23, 08010 Barcelona, Spain.
Carme
C
Rovira
Enrique
E
Pedroso
Anna
A
Grandas