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Preparation of novel meta and para substituted N-benzyl protected quinuclidine esters and their resolution with butyrylcholinesterase


Primožič, Ines; Bolant, Marijana; Ramić, Alma; Tomić, Srđanka
Preparation of novel meta and para substituted N-benzyl protected quinuclidine esters and their resolution with butyrylcholinesterase // Molecules, 17 (2012), 1; 786-795 doi:10.3390/molecules17010786 (međunarodna recenzija, članak, znanstveni)


Naslov
Preparation of novel meta and para substituted N-benzyl protected quinuclidine esters and their resolution with butyrylcholinesterase

Autori
Primožič, Ines ; Bolant, Marijana ; Ramić, Alma ; Tomić, Srđanka

Izvornik
Molecules (1420-3049) 17 (2012), 1; 786-795

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

Ključne riječi
Quinuclidin-3-ol ; esters ; resolution ; butyrylcholinesterase ; N-benzyl protected groups

Sažetak
Since the optically active quinuclidin-3-ol is an important intermediate in the preparation of physiologically or pharmacologically active compounds, new biocatalytic method for the production of chiral quinuclidin-3-ols was examined. Butyrylcholinesterase (BChE ; EC 3.1.1.8) was chosen as a biocatalyst in a preparative kinetic resolution of enantiomers. A series of racemic, (R)- and (S)- esters of quinuclidin-3-ol and acetic, benzoic, phthalic and isonicotinic acids were synthesized as well as their racemic and chiral, quaternary N-benzyl, meta and para N-bromobenzyl and meta and para N-methylbenzyl derivatives. After the resolution, all N-benzyl protected groups were successfully removed by catalytic transfer hydrogenation with ammonium formate (10% Pd-C).

Izvorni jezik
Engleski

Znanstvena područja
Kemija



POVEZANOST RADA


Projekt / tema
119-1191344-3121 - Sinteze i enzimske transformacije biološki aktivnih spojeva (Srđanka Tomić-Pisarović, )

Ustanove
Prirodoslovno-matematički fakultet, Zagreb

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
  • MEDLINE


Uključenost u ostale bibliografske baze podataka:


  • CA Search (Chemical Abstracts)


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