Pregled bibliografske jedinice broj: 15684
Biocatalytic deracemization of 1, 4-benzodiazepines in the synthesis of enantiopure serine
Biocatalytic deracemization of 1, 4-benzodiazepines in the synthesis of enantiopure serine // Helvetica chimica acta, 81 (1998), 1; 85-92 doi:10.1002/hlca.19980810110 (međunarodna recenzija, članak, znanstveni)
CROSBI ID: 15684 Za ispravke kontaktirajte CROSBI podršku putem web obrasca
Naslov
Biocatalytic deracemization of 1, 4-benzodiazepines in the synthesis of enantiopure serine
Autori
Avdagić, Amir ; Šunjić, Vitomir
Izvornik
Helvetica chimica acta (0018-019X) 81
(1998), 1;
85-92
Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni
Ključne riječi
Solid-phase synthesis. Amino-acids. Derivatives. Inhibitors
Sažetak
An efficient sterocontrolled synthesis of (S)-N-Cbz-serine and of its (R)-enantiomer is reported. Kinetic resolution of the easily available racemic 3-(hydroxymethyl)-1, 4-benzodiazepin-2-ones is performed in the key step via acetylation by the immobilized Mucor miehei lipase (Lipozyme IM) at 60. This method is characterized by high enantiomer purity of the intermediary alcohols (+)-8 and (+)-9 and acetates (-)-10 and (-)-11, as well as of the final products (S)- and (R)-N-Cbz-serine, simple recycling of the biocatalyst, complete recovery of 2-aminobenzophenones (3 and 4) and their recycling into production of 1, 4-benzodiazepines, and possibility to selectively racemize wrong enantiomers of the alcohols 8 and 9 in the presence of Amberlite CG 400.
Izvorni jezik
Engleski
Znanstvena područja
Kemija
Citiraj ovu publikaciju:
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
