Diastereoselective reduction of β-keto carbonyl compounds by cultured plant cells

The diastereoselective reduction of beta-keto carbonyl compounds such as 2-benzamidomethyl-3-oxobutanoates and 2-methyl-2-(2-propenyl)cyclopentan-1,3-dione by cultured cells of higher plants was investigated. The reduction of the 2-benzamidomethyl-3-oxobutanoates by Parthenocissus tricitspidata diastercoselectively produced the (2R,3S)-2-benzamidomethyl-3-hydroxybutanoates, whereas the reduction by Gossypium hirsultum gave the (2S,3S)-2-benzimidoinethyl-3-hydroxybutanoates. The (2R,3S)l (2S,3S) predominance in the reduction with Nicotiana tabacum, Glycine max, and Catharan thus roseus was reversed by the change in the structure of the alkoxyl group in the substrate. On the other hand, the reduction of 2-methyl-2-(2-propenyl)cyclopelitan-1,3-dione by P. tricuspidata produced (2R,3S)-3-hydroxy-2-methyl-2-(2-propenyl)cyclopent in-1-one, whereas the reaction by N. tabacum, G. max, C roseus' and G. hirsuatum gave (2S,3S)-3-hydroxy-2-methyl-2-(2-propenyl)cyclopentan-1-one. (c) 2006 Elsevier Ltd. All rights reserved.