Asymmetric reduction of 1-(benzoazol-2-ylsulfanyl)propan-2-ones using whole cells of Mortierella isabellina, Debaryomyces hansenii, Geotrichum candidum and Zygosaccharomyces rouxii

作者：Borowiecki Pawel; Wloczewska Malgorzata; Ochal Zbigniew^*

来源：Journal of Molecular Catalysis B: Enzymatic , 2014, 109: 9-16.

DOI：10.1016/j.molcatb.2014.07.015

• Biocatalysis
• Bioreduction
• 1-(Benzoazol-2-ylsulfanyl)propan-2-ones

Growing cells of four fungal strains were used in reduction of 1-(benzoazol-2-ylsulfanyl)propan-2-ones 3a-c to corresponding (R)-(+)-1-(benzoazol-2-ylsulfanyl)propan-2-ols (R)-(+)-4a-c. All of the investigated yeast strains displayed a very high activity toward prochiral ketones 3a-c converting them to the desired alcohols after relatively short reaction time (1-3.5 h). The biotransformation products were isolated with moderate to good yields (45-89%) and in highly enantioenriched forms (94-99% ee). Stereoselective bioreduction of 1-(1H-benzimidazol-2-ylsulfanyl)propan-2-one 3a by D. hansenii DSM 3428 growing cells provided the respective (R)-alcohol with %26gt;99% yield, in reasonable 65% isolated yield and in a highly stereoselective manner (98% ee) after 3 h of cultivation. In the same culture, bioreduction of 1-(1,3-benzoxazol-2-ylsulfanyl)propan-2-one 3b led to a 76% yield, 65% isolated yield and very high 94% ee of the formed (R)-alcohol. Similar 1.5 h incubation of 1-(1,3-benzothiazol-2-ylsulfanyl)propan-2-one 3c in G. candidum LOCK 105 culture resulted in the corresponding (R)-alcohol preparation in moderate 45% isolated yield with excellent enantiomeric purity (99% ee).

• 出版日期2014-11