137028-97-8

Ketomethylenebestatin is a carba-analogue of the aminopeptidase (AP) inhibitor bestatin. This synthesis was carried out by a malonic ester alkylation with the suitably protected halomethyl ketone of (2S,3R)-AHPBA*), followed by a second alkylation with isobutyl bromide of the resulting 4-ketodiester, and subsequent decarboxylation and deprotection. Ketomethylenebestatin is 10 fold less effective as inhibitor of aminopeptidases than bestatin.