Stereo-Controlled Asymmetric Bioreduction of α,β-Dehydroamino Acid Derivatives

Autor: Bernhard Hauer, Kurt Faber, Mélanie Hall, Christoph K. Winkler, Clemens Stueckler, Melanie Bonnekessel, Klaus Zangger
Rok vydání: 2011
Předmět:
Zdroj: Advanced Synthesis & Catalysis. 353:1169-1173
ISSN: 1615-4150
DOI: 10.1002/adsc.201100042
Popis: α,β-Dehydroamino acid derivatives proved to be a novel substrate class for ene-reductases from the 'old yellow enzyme' (OYE) family. Whereas N-acylamino substituents were tolerated in the α-position, β-analogues were generally unreactive. For aspartic acid derivatives, the stereochemical outcome of the bioreduction using OYE3 could be controlled by variation of the N-acyl protective group to furnish the corresponding (S)- or (R)-amino acid derivatives. This switch of stereo-preference was explained by a change in the substrate binding, by exchange of the activating ester group, which was proven by 2 H-labelling experiments.
Databáze: OpenAIRE