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Halohydrin dehalogenase-catalysed synthesis of fluorinated aromatic chiral building blocks

Dokli, Irena; Milčić, Nevena; Marin, Petra; Svetec Miklenić, Marina; Sudar, Martina; Tang, Lixia; Findrik Blažević, Zvjezdana; Majerić Elenkov, Maja (2021) Halohydrin dehalogenase-catalysed synthesis of fluorinated aromatic chiral building blocks. Catalysis communications, 152 . ISSN 1566-7367

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Kinetic resolution of a series of fluorinated styrene oxide derivatives was studied using halohydrin dehalogenase. A mutant HheC-W249P catalysed nucleophilic ring-opening with azide and cyanide ions with excellent enantioselectivity (E-values up to >200), which gives access to various enantiopure β- substituted alcohols and epoxides. It was found that the enzyme tolerates substrates in concentrations over 50 mM. However, different side reactions were observed at elevated concentrations and with prolonged reaction time. The biocatalytic azidolysis and cyanolysis of racemic 4- trifluoromethylstyrene oxide were performed on preparative scale, affording (R)-2-azido-1-(4- trifluoromethyl- phenyl)-ethanol in 38% yield and 97% ee, and (S)-3-hydroxy-3-(4-trifluoromethyl- phenyl)- propionitrile in 30% yield and 98% ee.

Item Type: Article
Uncontrolled Keywords: biocatalysis ; epoxides ; halohydrin dehalogenase ; kinetic resolution ; β-substituted alcohols
Subjects: NATURAL SCIENCES > Chemistry
Divisions: Division of Organic Chemistry and Biochemistry
Project titleProject leaderProject codeProject type
Enzimska sinteza fluoriranih kiralnih građevnih blokovaMajerić-Elenkov, MajaIP-2018-01-4493HRZZ
Depositing User: Irena Dokli
Date Deposited: 25 Jan 2022 13:53
DOI: 10.1016/j.catcom.2021.106285

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