title: Biocatalytic synthesis of C3 chiral building blocks by chloroperoxidase-catalyzed enantioselective halo-hydroxylation and epoxidation in the presence of ionic liquids.
abstract: The optically active C3 synthetic blocks are remarkably versatile intermediates for the synthesis of numerous pharmaceuticals and agrochemicals. This work provides a simple and efficient enzymatic synthetic route for the environment-friendly synthesis of C3 chiral building blocks. Chloroperoxidase (CPO)-catalyzed enantioselective halo-hydroxylation and epoxidation of chloropropene and allyl alcohol was employed to prepare C3 chiral building blocks in this work, including (R)-2,3-dichloro-1-propanol (DCP*), (R)-2,3-epoxy-1-propanol (GLD*), and (R)-3-chloro-1-2-propanediol (CPD*). The ee values of the formed C3 chiral building blocks DCP*, CPD*, and glycidol were 98.1, 97.5, and 96.7%, respectively. Moreover, the use of small amount of imidazolium ionic liquid enhanced the yield efficiently due to the increase of solubility of hydrophobic organic substrates in aqueous reaction media, as well as the improvement of affinity and selectivity of CPO to substrate.
authors.affiliation: School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an, 710062, P.R. China.
authors.forename: Yan
authors.initials: Y
authors.lastname: Liu
authors.affiliation: School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an, 710062, P.R. China.
authors.forename: Yali
authors.initials: Y
authors.lastname: Wang
authors.affiliation: School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an, 710062, P.R. China.|Key Laboratory of Macromolecular Science of Shaanxi Province, Shaanxi Normal University, Xi'an, 710062, P.R. China.
authors.forename: Yucheng
authors.initials: Y
authors.lastname: Jiang
authors.affiliation: School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an, 710062, P.R. China.|Key Laboratory of Macromolecular Science of Shaanxi Province, Shaanxi Normal University, Xi'an, 710062, P.R. China.
authors.forename: Mancheng
authors.initials: M
authors.lastname: Hu
authors.affiliation: School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an, 710062, P.R. China.|Key Laboratory of Macromolecular Science of Shaanxi Province, Shaanxi Normal University, Xi'an, 710062, P.R. China.
authors.forename: Shuni
authors.initials: S
authors.lastname: Li
authors.affiliation: School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an, 710062, P.R. China.|Key Laboratory of Macromolecular Science of Shaanxi Province, Shaanxi Normal University, Xi'an, 710062, P.R. China.
authors.forename: Quanguo
authors.initials: Q
authors.lastname: Zhai
mesh_terms: D055162:Biocatalysis; D002711:Chloride Peroxidase / Q000378:metabolism*; D002728:Chlorohydrins / Q000737:chemistry; D003176:Complement C3 / Q000378:metabolism*; D004852:Epoxy Compounds / Q000737:chemistry; D006900:Hydroxylation; D052578:Ionic Liquids / Q000737:chemistry*; D020005:Propanols / Q000737:chemistry; D000517:alpha-Chlorohydrin / Q000737:chemistry
chemical_list: D002728:Chlorohydrins; D003176:Complement C3; D004852:Epoxy Compounds; D052578:Ionic Liquids; D020005:Propanols; C006463:allyl alcohol; C076159:2,3-dichloro-1-propanol; D000517:alpha-Chlorohydrin; D002711:Chloride Peroxidase; C004312:glycidol
keywords: C3 chiral building blocks; asymmetric synthesis; chloroperoxidase; imidazolium ionic liquids