Comparative study in the asymmetric bioreduction of ketones by plant organs and undifferentiated cells.

ALEJANDRO A. ORDEN; FABRICIO R. BISOGNO; OSCAR S. GIORDANO; MARCELA KURINA SANZ

JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC

Elsevier

Año: 2008 vol. 51 p. 49 - 55

1381-1177

Stereoselective reduction of prochiral ketones was studied by using both cell cultures and wild tissues of various endemic plant species.Dedifferentiated cell cultures of Baccharis crispa reduced regioselectively, with excellent stereocontrol, and in an anti-Prelog manner the methylketone moiety of a diketone, meanwhile Tessaria absinthioides cell cultures yielded the other antipode of the secondary alcohol with an opticalpurity higher than 98% ee. Therefore, it is possible to prepare the S and R isomers of a secondary alcohol by reduction of the correspondingprochiral ketone with these two biocatalysts. Moreover, significant differences in the reductive capacity of cell cultures and differentiated tissuesof the same plant species were found. This fact allows improving the yields and optical purities and, even more interesting, obtaining the antipodeof a secondary alcohol with the same plant species by using alternatively both biocatalytic systems.