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Utilice este identificador para citar o enlazar este documento: https://ria.asturias.es/RIA/handle/123456789/13985


Título: Sequential two-step stereoselective amination of allylic alcohols through combination of laccases and amine transaminases
Autores: Albarrán Velo, Jesús
Lavandera, Iván
Gotor Fernández, Vicente
Palabras Claves: Química orgánica
Bioorgánica
Enzima
Estereoselectiva
Amina
Quiral
Cascada
Secuencial
Lacasa
Transaminasa
Biocatálisis
Fecha Edición: 26-Nov-2019
Editor: Wiley-VCH
Cita Bibliográfica: Albarrán Velo J., Lavandera I., Gotor Fernández, V. Sequential two-step stereoselective amination of allylic alcohols through combination of laccases and amine transaminases. ChemBioChem. 2020; 21 (1-2):200-211
Resumen: 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 oxyradical 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.
Descripción : Artículo de investigación destinado a la obtención de aminas alílicas enantioenriquecidas mediante el desarrollo de un proceso en cascada secuencial multienzimática
URI: https://ria.asturias.es/RIA/handle/123456789/13985
Aparece en las Colecciones:Química

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