title: Novel and highly effective chemoenzymatic synthesis of (2R)-2-[4-(4-cyano-2-fluorophenoxy)phenoxy]butylpropanoate based on lipase mediated transesterification.
abstract: (2R)-2-[4-(4-Cyano-2-fluorophenoxy)phenoxy]butylpropanoate (cyhalofop-butyl, CyB) was synthesized by a chemoenzymatic route involving enantioselective transesterification with Candida antarctica lipase B (Novozym 435). The optimum organic solvent, acyl donor, a ( w ), reaction temperature and shaking rate for the transesterification were acetonitrile, n-butanol, 0.11, 45°C and 200 rpm, respectively. Under the optimum conditions, the maximum substrate conversion and the enantiomeric purity of the product were 96.9 and >99%, respectively. The total yield and enantiomeric purity of CyB by this chemoenzymatic synthesis were 60.4 and >99%, respectively; 15.3 and 21% higher than that of the traditional way (45 and 78%).
authors.affiliation: Department of Pharmaceutical Engineering, School of Medical Engineering, Hefei University of Technology, Hefei, 230009, Anhui, PR China. zhugenlin87@sohu.com
authors.forename: Genlin
authors.initials: G
authors.lastname: Zhu
authors.forename: Risheng
authors.initials: R
authors.lastname: Yao
authors.forename: Huixia
authors.initials: H
authors.lastname: Zhu
authors.forename: Huai
authors.initials: H
authors.lastname: Wang
mesh_terms: D000097:Acetonitriles / Q000378:metabolism; D001709:Biotechnology / Q000379:methods; D002073:Butanes / Q000138:chemical synthesis* / Q000378:metabolism*; D000440:Butanols / Q000378:metabolism; D002175:Candida / Q000201:enzymology; D004800:Enzymes, Immobilized / Q000378:metabolism; D004951:Esterification; D005656:Fungal Proteins; D008049:Lipase / Q000378:metabolism*; D009570:Nitriles / Q000138:chemical synthesis* / Q000378:metabolism*; D013696:Temperature
chemical_list: D000097:Acetonitriles; D002073:Butanes; D000440:Butanols; D004800:Enzymes, Immobilized; D005656:Fungal Proteins; D009570:Nitriles; C501583:cyhalofop-butyl; C093667:Novozyme 435; D008049:Lipase; C032159:acetonitrile