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Design and Synthesis of Novel Fluoropeptidomimetics as Potential Mimics of the Transition State during Peptide Hydrolysis

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journal contribution
posted on 11.01.2003, 00:00 authored by Subhash C. Annedi, Weiyong Li, Sheeba Samson, Lakshmi P. Kotra
α-Fluoroamino acids were targeted in our ongoing efforts to design novel fluoropeptidomimetics (1) as potential protease inhibitors. α-Fluoroglycine derivative (2) and α-fluoro-β-aminoethanethiol derivatives (39) were synthesized for the first time en route to obtain the peptidomimetic moiety 1. The stability of 29 was investigated under organic as well as aqueous conditions. The stability of 39 under acidic and basic conditions, the effect of substitution at C-2 position, and potential biological activities are discussed.