Next Article in Journal
Recent Development of Non-Peptide GnRH Antagonists
Previous Article in Journal
Agarwood Essential Oil Displays Sedative-Hypnotic Effects through the GABAergic System
Previous Article in Special Issue
One-Step Partially Purified Lipases (ScLipA and ScLipB) from Schizophyllum commune UTARA1 Obtained via Solid State Fermentation and Their Applications
Article Menu
Issue 12 (December) cover image

Export Article

Open AccessArticle
Molecules 2017, 22(12), 2189; doi:10.3390/molecules22122189

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.
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)
View Full-Text   |   Download PDF [1046 KB, uploaded 9 December 2017]   |  

Abstract

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
Figures

This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

Scifeed alert for new publications

Never miss any articles matching your research from any publisher
  • Get alerts for new papers matching your research
  • Find out the new papers from selected authors
  • Updated daily for 49'000+ journals and 6000+ publishers
  • Define your Scifeed now

SciFeed Share & Cite This Article

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.

Show more citation formats Show less citations formats

Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top