Microbial synthesis of chiral amines by (R)-specific transamination with Arthrobacter sp. KNK168.
Arthrobacter sp. KNK168 shows (R)-enantioselective transaminase [(R)-transaminase] activity, which converts prochiral ketones into the corresponding chiral (R)-amines in the presence of an amino donor. The cultural conditions and reaction conditions for asymmetric synthesis of chiral amines with this microorganism were examined. The transaminase was inducible, and its production was enhanced by the addition of sec-butylamine and 3-amino-2,2-dimethylbutane to the culture medium. (R)-1-Phenylethylamine was a good amino donor for amination of 3,4-dimethoxyphenylacetone with Arthrobacter sp. KNK168. Under the optimum conditions, 126 mM (R)-3,4-dimethoxyamphetamine (DMA) [>99% enantiomeric excess (ee)] was synthesized from 154 mM 3,4-dimethoxyphenylacetone and 154 mM (R)-1-phenylethylamine through the whole cell reaction with an 82% conversion yield. (R)-Enantiomers of other amines, such as (R)-4-methoxyamphetamine, (R)-1-(3-hydroxyphenyl)ethylamine and (R)-1-(3-hydroxyphenyl)ethylamine, were also synthesized from the corresponding carbonyl compounds through asymmetric amination with Arthrobacter sp. KNK168.
Iwasaki
A
A
Life Science Research Laboratories, Life Science RD Center, Corporate Research and Development Division, Kaneka Corporation, 1-8, Miyamae-machi, Takasago-cho, Takasago, Hyogo, 676-8688, Japan. Akira_Iwasaki@kn.kaneka.co.jp
Yamada
Y
Y
Kizaki
N
N
Ikenaka
Y
Y
Hasegawa
J
J
D000096:Acetone / Q000031:analogs & derivatives / Q000378:metabolism; D000588:Amines / Q000378:metabolism*; D000662:Amphetamines / Q000378:metabolism; D001173:Arthrobacter / Q000254:growth & development / Q000378:metabolism*; D001711:Biotransformation; D002073:Butanes / Q000378:metabolism; D002082:Butylamines / Q000378:metabolism; D002851:Chromatography, High Pressure Liquid; D003470:Culture Media / Q000737:chemistry; D004790:Enzyme Induction; D007659:Ketones / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D010627:Phenethylamines / Q000378:metabolism; D013237:Stereoisomerism; D000637:Transaminases / Q000378:metabolism; D014439:Tyramine / Q000378:metabolism
C488390:3,4-dimethoxyphenylacetone; D000588:Amines; D000662:Amphetamines; D002073:Butanes; D002082:Butylamines; D003470:Culture Media; D007659:Ketones; D010627:Phenethylamines; C014500:3,4-dimethoxyamphetamine; D000096:Acetone; D000637:Transaminases; C033198:1-phenethylamine; C028169:3-tyramine; C100230:4-methoxyamphetamine; D014439:Tyramine