405-46-9Relevant academic research and scientific papers
Asymmetric Synthesis of Chiral Halogenated Amines using Amine Transaminases
Dawood, Ayad W. H.,de Souza, Rodrigo O. M. A.,Bornscheuer, Uwe T.
, p. 951 - 955 (2018/02/12)
Amine transaminases (ATAs) are versatile and industrially relevant biocatalysts that catalyze the transfer of an amine group from a donor to an acceptor molecule. Asymmetric synthesis from a prochiral ketone is the most preferred route to the desired amine product, as it is obtainable in a theoretical yield of 100 %. In addition to the requirement of active and enantioselective ATAs, the choice of a suitable amine donor is also important to save costs and to avoid additional enzymes to shift the equilibrium and/or to recycle the cofactors. In this work, we identified suitable (R)- and (S)-ATAs from Aspergillus fumigatus and Silicibacter pomeroyi, respectively, to afford a set of halogen-substituted derivatives of brominated or chlorinated 1-phenyl-2-propanamine, 4-phenylbutan-2-amine, and 1-(3-pyridinyl)ethanamine. Optimization of the donor–acceptor ratio enabled application of isopropylamine as an amine donor, which resulted in high conversions and amines with 73–99 % ee.
Enzymatic enantiomeric resolution of phenylethylamines structurally related to amphetamine
Munoz, Lourdes,Rodriguez, Anna M.,Rosell, Gloria,Bosch, M. Pilar,Guerrero, Angel
experimental part, p. 8171 - 8177 (2012/01/04)
Both enantiomers of several phenylethylamines, structurally related to amphetamine, have been prepared in good yields and excellent enantiomeric purity by enzymatic kinetic resolution using CAL-B and ethyl methoxyacetate as the acyl donor. In the case of the 4-hydroxyderivative of amphetamine (compound 4i), the S enantiomer racemized possibly in a dynamic kinetic resolution (DKR) under the enzymatic conditions used. The Royal Society of Chemistry 2011.
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