Wydział Chemii

Tomasz Janeczko

Jadwiga Dmochowska-Gładysz

Agata Białońska

Zbigniew Ciunik

2006

Biocatalysis and Biotransformation

24

458-463

10.1080/10242420601100214

Naukowa

Angielski

Artykuł

The biotransformations of (R)-(−)-methyloctalone and (S)-(+)-methyloctalone were investigated using Chaetomium sp.1 KCH 6651 and Didymosphaeria igniaria KCH 6670 as biocatalysts, yielding mostly 6β- and 7β-hydroxy derivatives. During the incubation of (R)-methyloctalone with the Chaetomium sp.1 culture, three products were obtained: the trans-7β-hydroxy derivative in 50% yield, trans-6β-hydroxy derivative in 30% yield and cis-8α-hydroxy derivative in 6% yield. The (S)-enone was hydroxylated mainly in the 6α-position (with 60% yield). 6β- and 7β-hydroxy derivatives are new compounds, not previously described in the literature. The biotransformation of the two enantiomers of methyloctalone with D. igniaria also afforded monohydroxy derivatives. In both cases the main product of transformation was the allylic hydroxy derivative (27–35% yield). D. igniaria transformed the (R)-methyloctalone more rapidly whereas Chaetomium sp. 1 preferred the (S)-methyloctalone.

biotransformations, bicyclic enones, Chaetomium sp, Didymosphaeria igniaria, Hydroxylation, enantiomeric resolution

https://doi.org/10.1080/10242420601100214