Stereoselective Formation of a Functionalized Dipeptide Isostere by Zinc Carbenoid-Mediated Chain Extension†

…, CR Theberge, TJ Henderson, CK Zercher…

Index: Lin, Weimin; Theberge, Cory R.; Henderson, Timothy J.; Zercher, Charles K.; Jasinski, Jerry; Butcher, Ray J. Journal of Organic Chemistry, 2009 , vol. 74, # 2 p. 645 - 651

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Citation Number: 10

Abstract

The application of a zinc carbenoid-mediated chain-extension reaction to a functionalized peptide isostere is reported. The cleavage site of human CVM protease was utilized as a target for testing the synthetic methodology. The utility of this chain-extension reaction is demonstrated in the preparation of an amino acid-derived α-unsubstituted γ-keto ester, which is incorporated into a framework that mimics a tetrapeptide. The identification of a ...