Peptidic Aldehydes Based on α- and β-Amino Acids: Synthesis, Inhibition of m-Calpain, and Anti-Cataract Properties

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Contents Vol 57(9)

doi:10.1071/CH04080

Peptidic Aldehydes Based on α- and β-Amino Acids: Synthesis, Inhibition of m-Calpain, and Anti-Cataract Properties

Richard J. Payne ^A, Karina M. Brown ^A, James M. Coxon ^A, James D. Morton ^B, Hannah Yun-Young Lee ^B, Andrew D. Abell ^A ^C

^A Department of Chemistry, University of Canterbury, Christchurch, New Zealand.
^B Animal and Food Sciences Division, Lincoln University, Canterbury, New Zealand.
^C Author to whom correspondence should be addressed (e-mail: andrew.abell@canterbury.ac.nz).





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Australian Journal of Chemistry 57(9) 877–884 http://dx.doi.org/10.1071/CH04080
Submitted: 23 March 2004 Accepted: 25 June 2004 Published online: 1 September 2004

Abstract

We present a new synthesis of SJA6017 (a potent m-calpain inhibitor) and its adaptation in order to prepare analogues in which the constituent Leu and Val residues are systematically replaced with their corresponding β-amino acids and/or the N-terminal fluorophenylsulfonyl group is replaced by a water solubilizing N-pyridin-3-ylmethoxycarbonyl group. All compounds have been assayed against m-calpain, and the best inhibitor, SJA6017, has been shown to inhibit the development of opacity in a lens culture system design to mimic cataract.