Ontology highlight
ABSTRACT:
SUBMITTER: Xu GG
PROVIDER: S-EPMC2844255 | biostudies-literature | 2010 Feb
REPOSITORIES: biostudies-literature
Xu Guoyan G GG Etzkorn Felicia A FA
Organic letters 20100201 4
A convergent synthesis of alpha-ketoamide inhibitors of Pin1 is described. An alpha-hydroxyorthothioester derivative of Ser was reacted directly with an amine synthon. The reaction was catalyzed by HgO and HgCl(2) to form alpha-hydroxyamide. Thus, hydrolysis and coupling were combined in one step with 80% yield. Two diastereomers of a phospho-Ser-Pro alpha-ketoamide analogue were synthesized. The IC(50) values of 100 and 200 microM were surprisingly weak for Pin1 peptidyl prolyl isomerase. ...[more]