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

FABRICIO R. BISOGNO

ADVANCED SYNTHESIS & CATALYSIS (PRINT)

WILEY-V C H VERLAG GMBH

Año: 2009 vol. 351 p. 1842 - 1842

1615-4150

font size="2" face="AdvTTR"> 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,