Tags

Type your tag names separated by a space and hit enter

Efficient biocatalytic synthesis of (R)-[3,5-bis(trifluoromethyl)phenyl] ethanol by a newly isolated Trichoderma asperellum ZJPH0810 using dual cosubstrate: ethanol and glycerol.
Appl Microbiol Biotechnol 2013; 97(15):6685-92AM

Abstract

(R)-[3,5-bis(trifluoromethyl)phenyl] ethanol is a crucial intermediate for the synthesis of Aprepitant. An efficient biocatalytic process for (R)-[3,5-bis(trifluoromethyl)phenyl] ethanol was developed via the asymmetric reduction of 3,5-bis(trifluoromethyl) acetophenone, catalyzed by whole cells of newly isolated Trichoderma asperellum ZJPH0810 using ethanol and glycerol as dual cosubstrate for cofactor recycling. A fungal strain ZJPH0810, showing asymmetric biocatalytic activity of 3,5-bis(trifluoromethyl) acetophenone to its corresponding (R)-[3,5-bis(trifluoromethyl)phenyl] ethanol, was isolated from a soil sample. Based on its morphological and physiological characteristics and internal transcribed spacer sequence, this isolate was identified as T. asperellum ZJPH0810, which afforded an NADH-dependent (R)-stereospecific carbonyl reductase and was a promising biocatalyst for the synthesis of (R)-[3,5-bis(trifluoromethyl)phenyl] ethanol. Some key reaction parameters involved in the bioreduction catalyzed by T. asperellum ZJPH0810 were subsequently optimized. The effectiveness of (R)-[3,5-bis(trifluoromethyl)phenyl] ethanol production was significantly enhanced by employing a novel dual cosubstrate-coupled system for cofactor recycling. The established efficient bioreduction system contained 50 mM of 3,5-bis(trifluoromethyl) acetophenone and 60 g l(-1) of resting cells, employing ethanol (6.0 %, v/v) and glycerol (0.5 %, v/v) as dual cosubstrate. The bioreduction was performed in distilled water medium, at 30 °C and 200 rpm. Under the above conditions, a best yield of 93.4 % was obtained, which is nearly a 3.5-fold increase in contrast to no addition of cosubstrate. The ee value of the product reached above 98 %. This biocatalytic process shows great potential in the production of (R)-[3,5-bis(trifluoromethyl)phenyl] ethanol, a valuable chiral building block in the pharmaceutical industry.

Authors+Show Affiliations

College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou, 310032, People's Republic of China.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

23700239

Citation

Li, Jun, et al. "Efficient Biocatalytic Synthesis of (R)-[3,5-bis(trifluoromethyl)phenyl] Ethanol By a Newly Isolated Trichoderma Asperellum ZJPH0810 Using Dual Cosubstrate: Ethanol and Glycerol." Applied Microbiology and Biotechnology, vol. 97, no. 15, 2013, pp. 6685-92.
Li J, Wang P, He JY, et al. Efficient biocatalytic synthesis of (R)-[3,5-bis(trifluoromethyl)phenyl] ethanol by a newly isolated Trichoderma asperellum ZJPH0810 using dual cosubstrate: ethanol and glycerol. Appl Microbiol Biotechnol. 2013;97(15):6685-92.
Li, J., Wang, P., He, J. Y., Huang, J., & Tang, J. (2013). Efficient biocatalytic synthesis of (R)-[3,5-bis(trifluoromethyl)phenyl] ethanol by a newly isolated Trichoderma asperellum ZJPH0810 using dual cosubstrate: ethanol and glycerol. Applied Microbiology and Biotechnology, 97(15), pp. 6685-92. doi:10.1007/s00253-013-4973-z.
Li J, et al. Efficient Biocatalytic Synthesis of (R)-[3,5-bis(trifluoromethyl)phenyl] Ethanol By a Newly Isolated Trichoderma Asperellum ZJPH0810 Using Dual Cosubstrate: Ethanol and Glycerol. Appl Microbiol Biotechnol. 2013;97(15):6685-92. PubMed PMID: 23700239.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Efficient biocatalytic synthesis of (R)-[3,5-bis(trifluoromethyl)phenyl] ethanol by a newly isolated Trichoderma asperellum ZJPH0810 using dual cosubstrate: ethanol and glycerol. AU - Li,Jun, AU - Wang,Pu, AU - He,Jun-Yao, AU - Huang,Jin, AU - Tang,Jun, Y1 - 2013/05/23/ PY - 2013/02/05/received PY - 2013/05/01/accepted PY - 2013/04/09/revised PY - 2013/5/24/entrez PY - 2013/5/24/pubmed PY - 2013/10/30/medline SP - 6685 EP - 92 JF - Applied microbiology and biotechnology JO - Appl. Microbiol. Biotechnol. VL - 97 IS - 15 N2 - (R)-[3,5-bis(trifluoromethyl)phenyl] ethanol is a crucial intermediate for the synthesis of Aprepitant. An efficient biocatalytic process for (R)-[3,5-bis(trifluoromethyl)phenyl] ethanol was developed via the asymmetric reduction of 3,5-bis(trifluoromethyl) acetophenone, catalyzed by whole cells of newly isolated Trichoderma asperellum ZJPH0810 using ethanol and glycerol as dual cosubstrate for cofactor recycling. A fungal strain ZJPH0810, showing asymmetric biocatalytic activity of 3,5-bis(trifluoromethyl) acetophenone to its corresponding (R)-[3,5-bis(trifluoromethyl)phenyl] ethanol, was isolated from a soil sample. Based on its morphological and physiological characteristics and internal transcribed spacer sequence, this isolate was identified as T. asperellum ZJPH0810, which afforded an NADH-dependent (R)-stereospecific carbonyl reductase and was a promising biocatalyst for the synthesis of (R)-[3,5-bis(trifluoromethyl)phenyl] ethanol. Some key reaction parameters involved in the bioreduction catalyzed by T. asperellum ZJPH0810 were subsequently optimized. The effectiveness of (R)-[3,5-bis(trifluoromethyl)phenyl] ethanol production was significantly enhanced by employing a novel dual cosubstrate-coupled system for cofactor recycling. The established efficient bioreduction system contained 50 mM of 3,5-bis(trifluoromethyl) acetophenone and 60 g l(-1) of resting cells, employing ethanol (6.0 %, v/v) and glycerol (0.5 %, v/v) as dual cosubstrate. The bioreduction was performed in distilled water medium, at 30 °C and 200 rpm. Under the above conditions, a best yield of 93.4 % was obtained, which is nearly a 3.5-fold increase in contrast to no addition of cosubstrate. The ee value of the product reached above 98 %. This biocatalytic process shows great potential in the production of (R)-[3,5-bis(trifluoromethyl)phenyl] ethanol, a valuable chiral building block in the pharmaceutical industry. SN - 1432-0614 UR - https://www.unboundmedicine.com/medline/citation/23700239/Efficient_biocatalytic_synthesis_of__R__[35_bis_trifluoromethyl_phenyl]_ethanol_by_a_newly_isolated_Trichoderma_asperellum_ZJPH0810_using_dual_cosubstrate:_ethanol_and_glycerol_ L2 - https://dx.doi.org/10.1007/s00253-013-4973-z DB - PRIME DP - Unbound Medicine ER -