Pretražite po imenu i prezimenu autora, mentora, urednika, prevoditelja

Napredna pretraga

Pregled bibliografske jedinice broj: 1112712

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
Halohydrin dehalogenase-catalysed synthesis of fluorinated aromatic chiral building blocks // Catalysis communications, 152 (2021), 106285, 5 doi:10.1016/j.catcom.2021.106285 (međunarodna recenzija, članak, znanstveni)


CROSBI ID: 1112712 Za ispravke kontaktirajte CROSBI podršku putem web obrasca

Naslov
Halohydrin dehalogenase-catalysed synthesis of fluorinated aromatic chiral building blocks

Autori
Dokli, Irena ; Milčić, Nevena ; Marin, Petra ; Svetec Miklenić, Marina ; Sudar, Martina ; Tang, Lixia ; Findrik Blažević, Zvjezdana ; Majerić Elenkov, Maja

Izvornik
Catalysis communications (1566-7367) 152 (2021); 106285, 5

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
biocatalysis ; epoxides ; halohydrin dehalogenase ; kinetic resolution ; β-substituted alcohols

Sažetak
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.

Izvorni jezik
Engleski

Znanstvena područja
Kemija, Biotehnologija



POVEZANOST RADA


Projekti:
HRZZ-IP-2018-01-4493 - Enzimska sinteza fluoriranih kiralnih građevnih blokova (EnzyFluor) (Majerić-Elenkov, Maja, HRZZ - 2018-01) ( POIROT)

Ustanove:
Prehrambeno-biotehnološki fakultet, Zagreb,
Institut "Ruđer Bošković", Zagreb,
Fakultet kemijskog inženjerstva i tehnologije, Zagreb

Citiraj ovu publikaciju

Dokli, Irena; Milčić, Nevena; Marin, Petra; Svetec Miklenić, Marina; Sudar, Martina; Tang, Lixia; Findrik Blažević, Zvjezdana; Majerić Elenkov, Maja
Halohydrin dehalogenase-catalysed synthesis of fluorinated aromatic chiral building blocks // Catalysis communications, 152 (2021), 106285, 5 doi:10.1016/j.catcom.2021.106285 (međunarodna recenzija, članak, znanstveni)
Dokli, I., Milčić, N., Marin, P., Svetec Miklenić, M., Sudar, M., Tang, L., Findrik Blažević, Z. & Majerić Elenkov, M. (2021) Halohydrin dehalogenase-catalysed synthesis of fluorinated aromatic chiral building blocks. Catalysis communications, 152, 106285, 5 doi:10.1016/j.catcom.2021.106285.
@article{article, year = {2021}, pages = {5}, DOI = {10.1016/j.catcom.2021.106285}, chapter = {106285}, keywords = {biocatalysis, epoxides, halohydrin dehalogenase, kinetic resolution, β-substituted alcohols}, journal = {Catalysis communications}, doi = {10.1016/j.catcom.2021.106285}, volume = {152}, issn = {1566-7367}, title = {Halohydrin dehalogenase-catalysed synthesis of fluorinated aromatic chiral building blocks}, keyword = {biocatalysis, epoxides, halohydrin dehalogenase, kinetic resolution, β-substituted alcohols}, chapternumber = {106285} }
@article{article, year = {2021}, pages = {5}, DOI = {10.1016/j.catcom.2021.106285}, chapter = {106285}, keywords = {biocatalysis, epoxides, halohydrin dehalogenase, kinetic resolution, β-substituted alcohols}, journal = {Catalysis communications}, doi = {10.1016/j.catcom.2021.106285}, volume = {152}, issn = {1566-7367}, title = {Halohydrin dehalogenase-catalysed synthesis of fluorinated aromatic chiral building blocks}, keyword = {biocatalysis, epoxides, halohydrin dehalogenase, kinetic resolution, β-substituted alcohols}, chapternumber = {106285} }

Časopis indeksira:


  • Current Contents Connect (CCC)
  • Web of Science Core Collection (WoSCC)
    • Science Citation Index Expanded (SCI-EXP)
    • SCI-EXP, SSCI i/ili A&HCI
  • Scopus


Citati





    Contrast
    Increase Font
    Decrease Font
    Dyslexic Font