Microbial resolution of 2-hydroxy-3-nitropropionic acid for synthesis of optically active isoserine.
The biocatalytic stereoselective hydrolysis of 2-hydroxy-3-nitropropionic acid esters was studied. Forty enzymes and three hundred microorganism strains were examined for their ability to hydrolyze ethyl 2-hydroxy-3-nitropropionic acid. Nocardia globerula IFO13150 gave n-butyl (R)-2-hydroxy-3-nitropropionate with a 92% enantiomeric excess (ee) and the corresponding carboxylic acid with a 92%ee, which was easily converted to (S)-isoserine, a useful beta-amino acid.
Yasohara
Y
Y
Fine Chemicals Research Laboratories, Kaneka Corporation, Takasago, Hyogo, Japan. Yoshihiko.Yasohara@kaneka.co.jp
Hasegawa
J
J
D001419:Bacteria / Q000378:metabolism*; D005658:Fungi / Q000378:metabolism*; D007773:Lactates / Q000737:chemistry*; D009574:Nitro Compounds / Q000737:chemistry*; D019906:Nuclear Magnetic Resonance, Biomolecular; D012694:Serine / Q000031:analogs & derivatives* / Q000096:biosynthesis* / Q000737:chemistry; D013045:Species Specificity; D013237:Stereoisomerism
C438913:2-hydroxy-3-nitropropionic acid; D007773:Lactates; D009574:Nitro Compounds; D012694:Serine; C072421:isoserine