- Development of an R-selective amine oxidase with broad substrate specificity and high enantioselectivity
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Amine oxidases are useful bio-catalysts for the synthesis of enantiomerically pure 1°, 2° and 3° chiral amines. Enzymes in this class (e.g., MAO-N from Aspergillus niger) reported previously have been shown to be highly S selective. Herein we report the development of an enantiocomplementary R-selective amine oxidase based on 6-hydroxy-D-nicotine oxidase (6-HDNO) with broadened substrate scope and high enantioselectivity. The engineered 6-HDNO enzyme has been applied to the preparative deracemisation of a range of racemic amines to yield S-configured products, for example, (S)-nicotine, in high ee. Nicotine rush: An R-selective amine oxidase based on 6-hydroxy-D-nicotine oxidase (6-HDNO) with broadened substrate scope and high enantioselectivity has been developed. The engineered 6-HDNO enzyme is applied to the preparative deracemization of a range of racemic amines to yield S-configured products, for example, (S)-nicotine, in high ee.
- Heath, Rachel S.,Pontini, Marta,Bechi, Beatrice,Turner, Nicholas J.
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p. 996 - 1002
(2014/05/06)
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- Renewable functionalized pyridines derived from microbial metabolites of the alkaloid (5)-nicotine
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(S)-Nicotine, which is present in concentrations of 2-8 % in dried leaves of certain tobacco plants, was used as a starting material for the biocatalytic production of renewable functionalized pyridines. Key microbial metabolites of (5)-nicotine, such as 6-hydroxy-(5)-nicotine and 4-[(6-hydroxypyridine)-3-yl]-4-oxobutyrate were used in subsequent chemical steps for the preparation of a wide variety of 2,5-di- or 2,3,5-tri-substituted pyridines.
- Roduit, Jean-Paul,Wellig, Alain,Kiener, Andreas
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p. 1687 - 1702
(2007/10/03)
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