Promiscuous Substrate Binding Explains the Enzymatic Stereo- and Regiocontrolled Synthesis of Enantiopure Hydroxy Ketones and Diols

作者：Kurina Sanz Marcela^*; Bisogno Fabricio R; Lavandera Ivan; Orden Alejandro A; Gotor Vicente

来源：Advanced Synthesis & Catalysis, 2009, 351(11-12): 1842-1848.

DOI：10.1002/adsc.200900218

• alcohol dehydrogenases
• diols
• hydrogen transfer
• hydroxy ketones
• quasi-irreversible reduction

Regio- and stereoselective reductions of several diketones to afford enantiopure hydroxy ketones or diols were accomplished using isolated alcohol dehydrogenases (ADHs). Results could be rationalised taking into account different (Promiscuous) substrate-binding modes in the active site of the enzyme. Furthermore, interesting natural cyclic diketones were also reduced with high regio- and stereoselectivity. Some of the 1,2- and 1,3-diketones used in this study were reduced by employing a low excess of the hydrogen donor (2-propanol) due to the quasi-irreversibility of these ADH-catalysed processes. Thus, using lower quantities of co-substrate, scale-up could be easily achieved.

• 出版日期2009-8