Asymmetric reduction of α,β-unsaturated carbonyl compounds with reductases from Nicotiana tabacum

Two reductases, p44 and p90, isolated from Nicotiana tabacum, catalyzed the asymmetric: reduction of alpha,beta-unsaturated carbonyl compounds. The p44 reductase reduced alpha-alkylated enones to (R)-ketones, while the reduction using the p90 reductase gave the (S)-ketones. The p90 reductase reduced beta-alkylated enones with excellent enantioselectivities to afford the (S)-ketones. On the other hand, the hydrogenation of the C-C double bond of 2-methylmaleimide with both enzymes gave (R)-2-methylsuccinimide. (C) 2004 Elsevier Ltd. All rights reserved.