Abstract
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.
Similar content being viewed by others
References
Anthony WS (1957) Resolution and rearrangement of α-methylhydrocinnamic acid and its 3,4-dimethoxy derivative. J Org Chem 22:33–35
Ayse H, Aldo J, Jaap AJ, Jonhannis AD (2000) Enantioselective oxidation of amphetamine by copper-containing quinoprotein amine oxidase from Escherichia coli and Klebsiella oxytoca. J Mol Catal B Enzym 11:81–88
Balkenhohl F, Ditrich K, Hauer B, Ladner W (1997) Optically active amines via lipase-catalyzed methoxyacetylation. J Prakt Chem 339:381–384
Iwasaki A, Yamada Y, Ikenaka Y, Hasegawa J (2003) Microbial synthesis of (R)- and (S)-3,4-dimethoxyamphetamines through stereoselective transamination. Biotechnol Lett 25:1843–1846
Jaeger KE, Liebeton K, Zonta A, Schimossek K, Reetz MK (1996) Biotechnological application of Pseudomonas aeruginosa lipase: efficient kinetic resolution of amines and alcohols. Appl Microbiol Biotechnol 46:99–105
Nakamichi K, Takeji S, Yuko Y, Tadashi S (1990) Asymmetric amination of 4-methoxyphenylacetone and its related compounds with microorganisms. Appl Microbiol Biotechnol 33:637–640
Reeve CD (1999) Resolution of chiral amines. WO9931264
Shin JS, Kim BG (1997) Kinetic resolution of α-methylbenzylamine with ω-transaminase screened from soil microorganisms: application of biphasic system to overcome product inhibition. Biotechnol Bioeng 55:348–358
Shin JS, Kim BG (1999) Asymmetric synthesis of chiral amines with ω-transaminase. Biotechnol Bioeng 65:206–211
Shin JS, Kim BC (2001) Comparison of the ω-transaminases from different microorganisms and application to production of chiral amines. Biosci Biotechnol Biochem 65:1782–1788
Shin JS, Kim BG, Liese A, Wandrey C (2001) Kinetic resolution of chiral amines with ω-transaminase using an enzyme-membrane reactor. Biotechnol Bioeng 73:179–187
Stirling DI (1992) The use of aminotransferases for the production of chiral acids and amines. In: Collins AN, Sheldrake GN, Crosby J (eds) Chirality in industry. Wiley, New York, pp 209–222
Yonaha K, Toyama S (1980) Aminobutyrate:α-ketoglutarate amino transferase from Pseudomonas sp. F-126: purification, crystallization and enzymologic properties. Arch Biochem Biophys 200:156–164
Yonaha K, Toyama S, Yasuda M, Soda M (1977) Properties of crystalline ω-amino acid transferase of Pseudomonas sp. F-126. Agric Biol Chem 41:1701–1706
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Iwasaki, A., Yamada, Y., Kizaki, N. et al. Microbial synthesis of chiral amines by (R)-specific transamination with Arthrobacter sp. KNK168. Appl Microbiol Biotechnol 69, 499–505 (2006). https://doi.org/10.1007/s00253-005-0002-1
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00253-005-0002-1