Chemoselective cysteine or disulfide modification <i>via</i> single atom substitution in chloromethyl acryl reagents
Lujuan Xu, Maria J. S. A. Silva, Pedro M. P. Góis, Seah Ling Kuan, Tanja Weil
Abstract
a simple and easily implemented one-pot reaction based on the coupling reaction between commercially available starting materials with different end-group functionalities (amino group or hydroxyl group). 2-Chloromethyl acrylamide reagents with an amide linkage favor selective modification at the cysteine site with fast reaction kinetics and near quantitative conversations. In contrast, 2-chloromethyl acrylate reagents bearing an ester linkage can undergo two successive Michael reactions, allowing the selective modification of disulfides bonds with high labeling efficiency and good conjugate stability.
Topics & Concepts
BioconjugationReagentChemistryCombinatorial chemistryCysteineAmideAcrylateConjugateDisulfide LinkageReactivity (psychology)AcrylamideOrganic chemistryCopolymerPolymerMathematicsMedicinePathologyMathematical analysisEnzymeAlternative medicineClick Chemistry and ApplicationsPeptidase Inhibition and AnalysisChemical Synthesis and Analysis