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

KURINA SANZ MB; BISOGNO FR; ORDEN AA; LAVANDERA I; GOTOR V

ADVANCED SYNTHESIS & CATALYSIS (PRINT)

Wiley

Año: 2009 vol. 351 p. 1842 - 1848

1615-4150

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.