The L-forms of racemic-N-protected-beta,gamma-unsaturated alpha-amino acid thioesters were found to be substrates for the subtilisin-catalysed hydrolysis to the corresponding acids. The D-enantiomer was continuously racemised in the presence of an organic base. The combined reactions in a biphasic system allowed the deracernisation of the amino acid derivatives based on a dynamic kinetic resolution. Excellent yields and enantioselectivities were achieved.

Chemo-enzymatic dynamic kinetic resolution of amino acid thioesters

AROSIO, DARIO;CALIGIURI, ANTONIO;D'ARRIGO, PAOLA;ROSSI, CRISTINA;SARACENO, CATERINA;SERVI, STEFANO;TESSARO, DAVIDE
2007

Abstract

The L-forms of racemic-N-protected-beta,gamma-unsaturated alpha-amino acid thioesters were found to be substrates for the subtilisin-catalysed hydrolysis to the corresponding acids. The D-enantiomer was continuously racemised in the presence of an organic base. The combined reactions in a biphasic system allowed the deracernisation of the amino acid derivatives based on a dynamic kinetic resolution. Excellent yields and enantioselectivities were achieved.
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11311/551760
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