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The first examination of a terminal α-fluorovinyl trigger in an amino acid decarboxylase active site is reported. To investigate the enantiospecificity of inactivation with this new AADC trigger, an enantioselective synthesis of l-α-(2‘Z-fluoro)vinyllysine and its d-antipode has been developed. Control of stereochemistry is achieved through introduction of the amino acid side chain via alkylation of a chiral vinylglycine-derived dienolate. Facial selectivity is conferred by a trans-2‘(β-naphthyl)-2‘-propylcyclohexyl ester auxiliary, available in both antipodal forms (Comins protocol). The alkylation employs a new electrophile, N-p-methoxybenzyl-N-(2‘-trimethylsilylethanesulfonyl)-4-iodobutylamine, for convergent installation of the lysine side chain. Vinyl to 2‘-fluorovinyl interconversion then provides l- and d-α-(2‘Z-fluoro)vinyllysine in 97-99% ee, as demonstrated by chiral HPLC. Both time-dependent enzyme kinetics and 19F NMR reveal striking differences in the behavior of these two antipodes in the ly...

Examination of the New α-(2‘Z-Fluoro)vinyl Trigger with Lysine Decarboxylase: The Absolute Stereochemistry Dictates the Reaction Course