Biocatalytic deracemization of 1, 4-benzodiazepines in the synthesis of enantiopure serine (CROSBI ID 81149)
Prilog u časopisu | izvorni znanstveni rad | međunarodna recenzija
Podaci o odgovornosti
Avdagić, Amir ; Šunjić, Vitomir
engleski
Biocatalytic deracemization of 1, 4-benzodiazepines in the synthesis of enantiopure serine
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.
Solid-phase synthesis. Amino-acids. Derivatives. Inhibitors
nije evidentirano
nije evidentirano
nije evidentirano
nije evidentirano
nije evidentirano
nije evidentirano