Synthesis of (R)-3,4-diaminobutanoic acid by desymmetrization of dimethyl 3-(benzylamino)glutarate through enzymatic ammonolysis.
Lipase B from Candida antarctica is shown to be a highly efficient catalyst for the desymmetrization of dimethyl 3-(benzylamino)glutarate (1) through aminolysis and ammonolysis reactions. Using this procedure, enantiopure monoamides are obtained in high yield. The synthetic value of these compounds is demonstrated by the preparation of an enantiopure nonnatural amino acid, i.e. (R)-3,4-diaminobutanoic acid [(+)-12].
López-García
Mónica
M
Departamento de Química Orgánica e Inorgánica, Facultad de Química, Universidad de Oviedo, Julián Clavería, 8, Spain.
Alfonso
Igancio
I
Gotor
Vicente
V
D000613:Aminobutyrates / Q000138:chemical synthesis*; D002175:Candida / Q000201:enzymology*; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods; D008049:Lipase / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D000644:Quaternary Ammonium Compounds / Q000737:chemistry*; D013237:Stereoisomerism
C474938:3,4-diaminobutanoic acid; D000613:Aminobutyrates; D000644:Quaternary Ammonium Compounds; D008049:Lipase