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Bioorg Med Chem Lett. 1999 Jan 18;9(2):139-40.

The synthesis of ketomethylene pseudopeptide analogues of dipeptide aldehyde inhibitors of calpain.

Author information

1
Hoechst Marion Roussel, Inc., Bridgewater, N.J. 08807, USA.

Abstract

The ketomethylene phenylalanal and alanal analogues of Cbz-Val-Phe-H and Cbz-Val-Ala-H have been prepared and the Ki values versus chicken gizzard smooth muscle calpain were determined. The ketomethylene isosteres were significantly less potent than the corresponding dipeptide aldehydes, and this loss in activity is attributed to the absence of a critical interaction between the P1-P2 amide bond and the peptide binding region of calpain.

PMID:
10021915
DOI:
10.1016/s0960-894x(98)00704-5
[Indexed for MEDLINE]

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