Promiscuous substrate-binding explains the enzymatic stereo- and regio-controlled synthesis of enantiopure hydroxy ketones and diols.

MARCELA KURINA-SANZ; FABRICIO R. BISOGNO; IVÁN LAVANDERA; ALEJANDRO A. ORDEN; VICENTE GOTOR

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 ketonesor 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.