β-Replacement reaction of serine-O-carbonate derivatives with thiols catalyzed by a pyridoxal model having an ionophore side-chain
Kazuyuki Miyashita,Hidenobu Murafuji,Hiroshi Iwaki,Eito Yoshioka,Takeshi Imanishi
Chemical Communications Pub Date : 07/30/2002 00:00:00 , DOI:10.1039/B206061B
Abstract

Serine-O-carbonate derivatives, including peptides having a serine-O-carbonate residue at the N-terminal position, are catalytically transformed into S-substituted cysteine derivatives employing the pyridoxal model having an ionophore function in the presence of Li+; this is the first artificial model mimicking cystathionine β-synthase.

Graphical abstract: β-Replacement reaction of serine-O-carbonate derivatives with thiols catalyzed by a pyridoxal model having an ionophore side-chain