A double catalyst system (protease + base) was applied to the dynamic kinetic resolution (DKR) of isomeric 1- and 2-α-naphthyl-glycines and -alanines exploiting the in situ racemization of their thioesters. Due to the different C-acidity of the two sets of compounds, different experimental conditions have been devised to perform the simultaneous resolution/racemization process. In all cases, the racemic N-Boc-thioesters were converted into the aminoacids with an l-configuration almost quantitatively and with complete enantioselectivity.

Naphthyl-l-α-amino acids via chemo-enzymatic dynamic kinetic resolution

D'ARRIGO, PAOLA;CERIOLI, LORENZO;FIORATI, ANDREA;SERVI, STEFANO;TESSARO, DAVIDE
2012-01-01

Abstract

A double catalyst system (protease + base) was applied to the dynamic kinetic resolution (DKR) of isomeric 1- and 2-α-naphthyl-glycines and -alanines exploiting the in situ racemization of their thioesters. Due to the different C-acidity of the two sets of compounds, different experimental conditions have been devised to perform the simultaneous resolution/racemization process. In all cases, the racemic N-Boc-thioesters were converted into the aminoacids with an l-configuration almost quantitatively and with complete enantioselectivity.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11311/675351
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