Pregled bibliografske jedinice broj: 15698
Lipase-catalyzed acetylation of 3-substituted 2, 3-dihydro-1H-1, 4-benzodiazepin-2-ones : effect of temperature and conformation on enantioselectivity and configuration
Lipase-catalyzed acetylation of 3-substituted 2, 3-dihydro-1H-1, 4-benzodiazepin-2-ones : effect of temperature and conformation on enantioselectivity and configuration // Helvetica chimica acta, 81 (1998), 8; 1567-1582 doi:10.1002/hlca.19980810558 (međunarodna recenzija, članak, znanstveni)
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Naslov
Lipase-catalyzed acetylation of 3-substituted 2, 3-dihydro-1H-1, 4-benzodiazepin-2-ones : effect of temperature and conformation on enantioselectivity and configuration
Autori
Avdagić, Amir ; Lesac, Andreja ; Majer, Zsuzsa ; Hollosi, Miklos ; Šunjić, Vitomir
Izvornik
Helvetica chimica acta (0018-019X) 81
(1998), 8;
1567-1582
Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni
Ključne riječi
human-serum albumin; alpha-amino-acids; chiral 1; 4-benzodiazepin-2-ones; kinetic resolutions
Sažetak
Enantioselectivty of acetylation by vinyl acetate/AcOEt catalyzed by immobilized Candida antarctica lipase (Novozym 435) is studied for rac-3-(hydroxymethyl)-1, 4-benzodiazepin-2-ones 7, 9, 14 and for prochiral 3, 3-bis(hydroxymethyl) derivative 16. Enantiomeric excess is correlated with conformational properties of substrates as determined by DNMR and MM2 calculations. For racemic alcohols 7, 9, 14 and 20, preferred acetylation of the (3S)-enantiomers, present in solution in absolute (M)-conformation, was established ; only in prochiral diol 16 the CH2OH group in the (pro-R)-position is prevalently acetylated, presumably due to the binding to the enzyme, in absolute (P)-conformation.
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
