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

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...

Full description

Saved in:
Bibliographic Details
Published in:Advanced synthesis & catalysis 2009-08, Vol.351 (11-12), p.1842-1848
Main Authors: Kurina-Sanz, Marcela, Bisogno, Fabricio R., Lavandera, Iván, Orden, Alejandro A., Gotor, Vicente
Format: Article
Language:English
Subjects:
alcohol dehydrogenases
diols
hydrogen transfer
hydroxy ketones
quasi-irreversible reduction
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.200900218