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Stereo‐Controlled Asymmetric Bioreduction of α,β‐Dehydroamino Acid Derivatives
Author(s) -
Stueckler Clemens,
Winkler Christoph K.,
Hall Mélanie,
Hauer Bernhard,
Bonnekessel Melanie,
Zangger Klaus,
Faber Kurt
Publication year - 2011
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201100042
Subject(s) - chemistry , substrate (aquarium) , aspartic acid , stereochemistry , carboxylic acid , enzyme , amino acid , organic chemistry , biochemistry , oceanography , geology
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 stereopreference was explained by a change in the substrate binding, by exchange of the activating ester group, which was proven by 2 H‐labelling experiments.