Microbial synthesis of (R)- and (S)-3,4-dimethoxyamphetamines through stereoselective transamination.
Two soil isolates, Arthrobactersp. KNK168 and Pseudomonas sp. KNK425, aminated 3,4-dimethoxyphenylacetone in presence of sec-butylamine as an amino donor to yield 3,4-dimethoxyamphetamine (DMA) with different enantioselectivities. The former gave (R)-DMA (>99% e.e.) and the latter the (S)-isomer (>99% e.e.).
Iwasaki
Akira
A
Life Science Research Laboratories, Life Science RD Center, Kaneka Corporation, 1-8, Miyamae-machi, Yakasago-cho, Takasago, Hyogo 676-8688, Japan. Akira_Iwasaki@kn.kaneka.co.jp
Yamada
Yukio
Y
Ikenaka
Yasuhiro
Y
Hasegawa
Junzo
J
D000096:Acetone / Q000031:analogs & derivatives / Q000378:metabolism*; D000588:Amines / Q000737:chemistry / Q000378:metabolism*; D000662:Amphetamines / Q000737:chemistry / Q000378:metabolism*; D001173:Arthrobacter / Q000378:metabolism*; D011549:Pseudomonas / Q000378:metabolism*; D013045:Species Specificity; D013237:Stereoisomerism
C488390:3,4-dimethoxyphenylacetone; D000588:Amines; D000662:Amphetamines; C014500:3,4-dimethoxyamphetamine; D000096:Acetone