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A sequential two-step chemoenzymatic methodology has been described for the stereoselective synthesis of (3E)-4-(het)arylbut-3-en-2-amines in a highly selective manner and under mild reaction conditions. The approach consists in the oxidation of the corresponding alcohol precursors using the catalytic system composed by the laccase from Trametes versicolor and the oxy-radical TEMPO, followed by the asymmetric biotransamination of the corresponding ketone intermediates. Optimisation of the oxidation reaction, exhaustive amine transaminase screening for the biotransaminations and the compatibility of both enzymatic reactions have been deeply studied, searching for the design of a compatible sequential cascade. This synthetic strategy has been successfully achieved, the combination of enzymes displaying a broad substrate scope as 16 chiral amines have been obtained in moderate to good isolated yields (29-75% isolated yield) and excellent enantiomeric excess (94->99). Interestingly, both amine enantiomers can be achieved depending on the selectivity of the amine transaminase employed in the system.
This article was published in the following journal.
Name: Chembiochem : a European journal of chemical biology
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Alkyl compounds containing a hydroxyl group. They are classified according to relation of the carbon atom: primary alcohols, R-CH2OH; secondary alcohols, R2-CHOH; tertiary alcohols, R3-COH. (From Grant & Hackh's Chemical Dictionary, 5th ed)
A brominating agent that replaces hydrogen atoms in benzylic or allylic positions. It is used in the oxidation of secondary alcohols to ketones and in controlled low-energy brominations. (From Miall's Dictionary of Chemistry, 5th ed; Hawley's Condensed Chemical Dictionary, 12th ed,).
3'-Phosphoadenosine-5'-phosphosulfate. Key intermediate in the formation by living cells of sulfate esters of phenols, alcohols, steroids, sulfated polysaccharides, and simple esters, such as choline sulfate. It is formed from sulfate ion and ATP in a two-step process. This compound also is an important step in the process of sulfur fixation in plants and microorganisms.
Usually high-molecular-weight, straight-chain primary alcohols, but can also range from as few as 4 carbons, derived from natural fats and oils, including lauryl, stearyl, oleyl, and linoleyl alcohols. They are used in pharmaceuticals, cosmetics, detergents, plastics, and lube oils and in textile manufacture. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed)
A zinc-containing enzyme which oxidizes primary and secondary alcohols or hemiacetals in the presence of NAD. In alcoholic fermentation, it catalyzes the final step of reducing an aldehyde to an alcohol in the presence of NADH and hydrogen.