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Article

One-Pot Lipase-Catalyzed Enantioselective Synthesis of (R)-(−)-N-Benzyl-3-(benzylamino)butanamide: The Effect of Solvent Polarity on Enantioselectivity

1
The Center for Chemical Research, Autonomous University of Morelos State, Avenida Universidad 1001, Chamilpa, Cuernavaca 62210, Mexico
2
Departamento de Química, Centro de Investigación y de Estudios Avanzados, Avenida I.P.N. 2508, Ciudad de México 07360, Mexico
3
El Colegio Nacional, Luis Gonzáles Obregón 23, Centro Histórico, Ciudad de México 06020, Mexico
4
Department of Cell Engineering and Biocatalysis, Institute of Biotechnology, UNAM, Apartado Postal 510-3, Cuernavaca C.P. 62271, Mexico
*
Authors to whom correspondence should be addressed.
Molecules 2017, 22(12), 2189; https://doi.org/10.3390/molecules22122189
Received: 6 November 2017 / Revised: 28 November 2017 / Accepted: 4 December 2017 / Published: 9 December 2017
(This article belongs to the Special Issue Lipases and Lipases Modification)
The use of the solvent engineering has been applied for controlling the resolution of lipase-catalyzed synthesis of β-aminoacids via Michael addition reactions. The strategy consisted of the thermodynamic control of products at equilibrium using the lipase CalB as a catalyst. The enzymatic chemo- and enantioselective synthesis of (R)-(−)-N-benzyl-3-(benzylamino)butanamide is reported, showing the influence of the solvent on the chemoselectivity of the aza-Michael addition and the subsequent kinetic resolution of the Michael adduct; both processes are catalyzed by CalB and both are influenced by the nature of the solvent medium. This approach allowed us to propose a novel one-pot strategy for the enzymatic synthesis of enantiomerically enriched β-aminoesters and β-aminoacids. View Full-Text
Keywords: lipase promiscuity; aza-Michael addition; stereoselectivity; enantioselectivity; chemoselectivity; solvent engineering lipase promiscuity; aza-Michael addition; stereoselectivity; enantioselectivity; chemoselectivity; solvent engineering
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MDPI and ACS Style

Ortega-Rojas, M.A.; Rivera-Ramírez, J.D.; Ávila-Ortiz, C.G.; Juaristi, E.; González-Muñoz, F.; Castillo, E.; Escalante, J. One-Pot Lipase-Catalyzed Enantioselective Synthesis of (R)-(−)-N-Benzyl-3-(benzylamino)butanamide: The Effect of Solvent Polarity on Enantioselectivity. Molecules 2017, 22, 2189. https://doi.org/10.3390/molecules22122189

AMA Style

Ortega-Rojas MA, Rivera-Ramírez JD, Ávila-Ortiz CG, Juaristi E, González-Muñoz F, Castillo E, Escalante J. One-Pot Lipase-Catalyzed Enantioselective Synthesis of (R)-(−)-N-Benzyl-3-(benzylamino)butanamide: The Effect of Solvent Polarity on Enantioselectivity. Molecules. 2017; 22(12):2189. https://doi.org/10.3390/molecules22122189

Chicago/Turabian Style

Ortega-Rojas, Marina A., José D. Rivera-Ramírez, C. G. Ávila-Ortiz, Eusebio Juaristi, Fernando González-Muñoz, Edmundo Castillo, and Jaime Escalante. 2017. "One-Pot Lipase-Catalyzed Enantioselective Synthesis of (R)-(−)-N-Benzyl-3-(benzylamino)butanamide: The Effect of Solvent Polarity on Enantioselectivity" Molecules 22, no. 12: 2189. https://doi.org/10.3390/molecules22122189

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