| Identification | Back Directory | [Name]
ketomethylenebestatin | [CAS]
137028-97-8 | [Synonyms]
ketomethylenebestatin
(2R,5S,6R)-6-amino-5-hydroxy-2-(2-methylpropyl)-4-oxo-7-phenylheptanoic acid | [Molecular Formula]
C17H25NO4 | [MOL File]
137028-97-8.mol | [Molecular Weight]
307.39 |
| Hazard Information | Back Directory | [Description]
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. | [Uses]
Ketomethylenebestatin is an aminopeptidase (AP) inhibitor and an analog of the natural aminopeptidase inhibitor Bestatin (HY-B0134) with IC50 of 56 μM, 752 μM and 0.39 μM for AP-B, AP-M and Leu-AP, respectively[1]. | [References]
[1] Herranz, et al. Ketomethylenebestatin: synthesis and aminopeptidase inhibition. Archiv der Pharmazie 326.7 (1993): 395-398. DOI:10.1002/ardp.19933260705 |
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