Enzymatic asymmetric synthesis of alpha-methyl arylalkylamines and alpha-methyl arylalkylalcohols by arylalkyl acylamidases.
With the novel microbial enzyme, 'arylalkyl acylamidase', optically active alpha-methyl arylalkylamines and alpha-methyl arylalkylalcohols have been obtained through enantioselective hydrolysis of their racemic amides and esters. (S)-Enantiomers of 1-methylbenzylamine, 1-methyl-3-phenylpropylamine and 1-methyl-3-phenylpropanol of high optical purity (> 94% e.e.) were synthesized with the cells of Nocardia erythropolis IAM 1440 or Cellulomonas fimi AKU 671. (R)-Enantiomer of 1-methyl-3-phenylpropylamine and (S)-enantiomer of 1-methyl-2-phenylpropanol of high optical purity (> 95% e.e.) were synthesized with the crude preparation of arylalkyl acylamidase of Pseudomonas putida Sc2 AKU 881.
Ogawa
J
J
Department of Agricultural Chemistry, Kyoto University, Japan.
Shimizu
S
S
Yamada
H
H
D000150:Acinetobacter / Q000201:enzymology; D000192:Actinomycetales / Q000201:enzymology*; D000581:Amidohydrolases / Q000378:metabolism*; D001407:Bacillus / Q000201:enzymology; D001419:Bacteria / Q000201:enzymology*; D002082:Butylamines / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification; D003352:Corynebacterium / Q000201:enzymology; D007700:Kinetics; D009615:Nocardia / Q000201:enzymology; D010627:Phenethylamines / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification; D016958:Pseudomonas putida / Q000201:enzymology; D012240:Rhodococcus / Q000201:enzymology; D013045:Species Specificity; D013237:Stereoisomerism
D002082:Butylamines; D010627:Phenethylamines; D000581:Amidohydrolases; C077287:arylalkyl acylamidase