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. |