Halohydrin dehalogenase-catalysed synthesis of fluorinated aromatic chiral building blocks (CROSBI ID 291241)
Prilog u časopisu | kratko priopćenje | međunarodna recenzija
Podaci o odgovornosti
Dokli, Irena ; Milčić, Nevena ; Marin, Petra ; Svetec Miklenić, Marina ; Sudar, Martina ; Tang, Lixia ; Findrik Blažević, Zvjezdana ; Majerić Elenkov, Maja
engleski
Halohydrin dehalogenase-catalysed synthesis of fluorinated aromatic chiral building blocks
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.
biocatalysis ; epoxides ; halohydrin dehalogenase ; kinetic resolution ; β-substituted alcohols
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Podaci o izdanju
152
2021.
106285
5
objavljeno
1566-7367
1873-3905
10.1016/j.catcom.2021.106285