Asymmetric bioreduction of activated carbon-carbon double bonds using Shewanella yellow enzyme (SYE-4) as novel enoate reductase

作者：Iqbal Naseem; Rudroff Florian; Brige Ann; Van Beeumen Jozef; Mihovilovic Marko D^*

来源：Tetrahedron, 2012, 68(37): 7619-7623.

DOI：10.1016/j.tet.2012.05.092

• Enoate reductase
• Shewanella yellow enzyme
• Bioreduction
• Biocatalysis

Shewanella yellow enzyme (SYE-4), a novel recombinant enoate reductase, was screened against a variety of different substrates bearing an activated double bond, such as unsaturated cyclic ketones, diesters, and substituted imides. Dimethyl- and ethyl esters of 2-methylmaleic acid were selectively reduced to (R)-configured succinic acid derivatives and various N-substituted maleimides furnished the desired (R)-products in up to %26gt;99% enantiomeric excess. Naturally occurring (+)-carvone was selectively reduced to (-)-cis-dihydrocarvone and (-)-carvone was converted to the diastereomeric product, respectively. Overall SYE-4 proved to be a useful biocatalyst for the selective reduction of activated C=C double bonds and complements the pool of synthetic valuable enoate reductases.

• 出版日期2012-9-16