Identification of a newly isolated Sphingomonas sp. LZ1 and its application to biosynthesize chiral alcohols.
A strain LZ1, which showed efficient asymmetric reduction of 3,5-bis(trifluoromethyl) acetophenone to enantiopure (S)-[3,5-bis(trifluoromethyl)phenyl]ethanol, which is the key intermediate for the synthesis of a receptor antagonist and antidepressant, was isolated from a soil sample. Based on its morphological, 16S rDNA sequence, and phylogenetic analysis, the strain LZ1 was identified to be Sphingomonas sp. LZ1. To our knowledge, this is the first reported case of the species Sphingomonas exhibiting stricter S-enantioselectivity and its use for the asymmetric reduction of 3,5-bis(trifluoromethyl) acetophenone. Some key reaction parameters involved in the bioreduction catalyzed by whole cells of Sphingomonas sp. LZ1 were subsequently optimized, and the optimized conditions for the synthesis of (S)-[3,5-bis(trifluoromethyl)phenyl]ethanol were determined to be as follows: phosphate buffer pH 7.5, 70 mM of 3,5-bis(trifluoromethyl) acetophenone, 30 g/L of glucose as a co-substrate, 300 g (wet weight)/L of resting cell as the biocatalyst, and a reaction for 24 h at 30°C and 180 rpm. Under the above conditions, a best yield of 94% and an excellent enantiomeric excess of 99.6% were obtained, respectively. Sphingomonas sp. LZ1 could also asymmetrically reduce a variety of prochiral ketones to their corresponding optical alcohols with excellent enantioselectivity. These results indicated that Sphingomonas sp. LZ1 had a remarkable capacity to reduce 3,5-bis(trifluoromethyl)acetophenone to its corresponding (S)-[3,5-bis(trifluoromethyl)phenyl]ethanol, and might be a new potential biocatalyst for the production of valuable chiral alcohols in industry.
['Wang|Nengqiang|N|', 'Luo|Zhen|Z|', 'Li|Kaiqin|K|', 'Xu|Yingcui|Y|', 'Peng|Cheng|C|']
D000098:Acetophenones D000438:Alcohols D055162:Biocatalysis D006863:Hydrogen-Ion Concentration D007659:Ketones D010802:Phylogeny D012336:RNA, Ribosomal, 16S D020578:Sphingomonas D013237:Stereoisomerism D013379:Substrate Specificity D013696:Temperature
Sphingomonas sp. asymmetric reduction 3,5-bis(trifluoromethyl)acetophenone biocatalysis carbonyl reductase