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The importance of yeast old yellow enzymes is increasingly recognized for direct asymmetric reduction of ( E / Z )-citral to ( R )-citronellal. As one of the most performing old yellow enzymes, the enzyme OYE3 from Saccharomyces cerevisiae S288C exhibited complementary enantioselectivity for the reduction of ( E )-citral and ( Z )-citral, resulting in lower e.e. value of ( R )-citronellal in the reduction of ( E / Z )-citral. To develop a novel approach for the direct synthesis of enantio-pure ( R )-citronellal from the reduction of ( E / Z )-citral, the enzyme OYE3 was firstly modified by semi-rational design to improve its ( R )-enantioselectivity. The OYE3 variants W116A and S296F showed strict ( R )-enantioselectivity in the reduction of ( E )-citral, and significantly reversed the ( S )-enantioselectivity in the reduction of ( Z )-citral. Next, the double substitution of OYE3 led to the unique variant S296F/W116G, which exhibited strict ( R )-enantioselectivity in the reduction of ( E )-citral and ( E / Z )-citral, but was not active on ( Z )-citral. Relying on its capability discriminating ( E )-citral and ( Z )-citral, a new cascade reaction catalyzed by the OYE3 variant S296F/W116G and glucose dehydrogenase was developed, providing the enantio-pure ( R )-citronellal and the retained ( Z )-citral after complete reduction of ( E )-citral.

Engineering of Yeast Old Yellow Enzyme OYE3 Enables Its Capability Discriminating of (E)-Citral and (Z)-Citral