Synthesis of enantiomerically pure trans-(1R,2R)- and cis-(1S,2R)-1-amino-2-indanol by lipase and omega-transaminase.
Syntheses of trans-(1R,2R) and cis-(1S,2R)-1-amino-2-indanol (AI) were accomplished by a series of enantioselective enzymatic reactions using lipase and transaminase (TA). Lipase catalysed enantioselective hydrolysis of 2-acetoxyindanone was employed to prepare (R)-2-hydroxy indanone (HI). trans-AI (5 mM) (de > 98%) was produced from 20 mM (R)-2- HI using omega-TA and 50 mM (S)-1-aminoindan as an amino donor in water-saturated ethyl acetate. For the production of cis-AI, the diastereomeric (2R)-AI was synthesized from (R)-2-HI using reductive amination, and the kinetic resolution was performed with omega-TA. The enantioselectivity of omega-TA for (2R)-AI was increased to 22.1 in the presence of 5% gamma-cyclodextrin. cis-AI (15.4 mM) (96% de) was obtained from 40 mM (2R)-AI using 30 mM pyruvate and omega-TA (25 mg) in 10 mL of 100 mM phosphate buffer (pH 7.0).
Yun
Hyungdon
H
Laboratory of Biotechnology and Biomaterials, Institute of Molecular Biology and Genetics, School of Chemical and Biological Engineering, Seoul National University, Seoul, 151-742, Korea.
Kim
Juhan
J
Kinnera
Koteshwar
K
Kim
Byung-Gee
BG
D007189:Indans / Q000737:chemistry*; D008049:Lipase / Q000737:chemistry*; D013237:Stereoisomerism; D000637:Transaminases / Q000737:chemistry*
D007189:Indans; C116915:aminoindanol; D000637:Transaminases; D008049:Lipase