Kinetics and Mechanisms of Reactions of Thiol, Thiono, and Dithio Analogues of Carboxylic Esters with Nucleophiles.

Synergy between catalysts : enzymes and bases. DKR of non-natural amino acids derivatives

Racemic natural and non-natural N-Boc-amino acid thioesters undergo enzyme-catalyzed ammoniolysis and aminolysis with concomitant base-catalyzed racemization of the non-transformed D-enantiomer with the formation of the corresponding L-amides in good yields and excellent enantiomeric purity all above 98% ee. This is the first example of a dynamic kinetic resolution of amino acid derivatives with amides formation.

Š. Horvat

Papers

Kinetics of aminolysis for 1-thio-β- D-glucopyranosyl esters of N-acylalanines