One-Pot Lipase-Catalyzed Enantioselective Synthesis of (R)-(−)-N-Benzyl-3-(benzylamino)butanamide: The Effect of Solvent Polarity on Enantioselectivity
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- an...
| Main Authors: | , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2017-12-01
|
| Series: | Molecules |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1420-3049/22/12/2189 |
| _version_ | 1818912467105873920 |
|---|---|
| author | Marina A. Ortega-Rojas José Domingo Rivera-Ramírez C. Gabriela Ávila-Ortiz Eusebio Juaristi Fernando González-Muñoz Edmundo Castillo Jaime Escalante |
| author_facet | Marina A. Ortega-Rojas José Domingo Rivera-Ramírez C. Gabriela Ávila-Ortiz Eusebio Juaristi Fernando González-Muñoz Edmundo Castillo Jaime Escalante |
| author_sort | Marina A. Ortega-Rojas |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-12-19T23:15:03Z |
| format | Article |
| id | doaj.art-7b43050cf08949a78afd97b561e489d6 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-19T23:15:03Z |
| publishDate | 2017-12-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-7b43050cf08949a78afd97b561e489d62022-12-21T20:02:08ZengMDPI AGMolecules1420-30492017-12-012212218910.3390/molecules22122189molecules22122189One-Pot Lipase-Catalyzed Enantioselective Synthesis of (R)-(−)-N-Benzyl-3-(benzylamino)butanamide: The Effect of Solvent Polarity on EnantioselectivityMarina A. Ortega-Rojas0José Domingo Rivera-Ramírez1C. Gabriela Ávila-Ortiz2Eusebio Juaristi3Fernando González-Muñoz4Edmundo Castillo5Jaime Escalante6The Center for Chemical Research, Autonomous University of Morelos State, Avenida Universidad 1001, Chamilpa, Cuernavaca 62210, MexicoThe Center for Chemical Research, Autonomous University of Morelos State, Avenida Universidad 1001, Chamilpa, Cuernavaca 62210, MexicoDepartamento de Química, Centro de Investigación y de Estudios Avanzados, Avenida I.P.N. 2508, Ciudad de México 07360, MexicoDepartamento de Química, Centro de Investigación y de Estudios Avanzados, Avenida I.P.N. 2508, Ciudad de México 07360, MexicoDepartment of Cell Engineering and Biocatalysis, Institute of Biotechnology, UNAM, Apartado Postal 510-3, Cuernavaca C.P. 62271, MexicoDepartment of Cell Engineering and Biocatalysis, Institute of Biotechnology, UNAM, Apartado Postal 510-3, Cuernavaca C.P. 62271, MexicoThe Center for Chemical Research, Autonomous University of Morelos State, Avenida Universidad 1001, Chamilpa, Cuernavaca 62210, MexicoThe 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.https://www.mdpi.com/1420-3049/22/12/2189lipase promiscuityaza-Michael additionstereoselectivityenantioselectivitychemoselectivitysolvent engineering |
| spellingShingle | Marina A. Ortega-Rojas José Domingo Rivera-Ramírez C. Gabriela Ávila-Ortiz Eusebio Juaristi Fernando González-Muñoz Edmundo Castillo Jaime Escalante One-Pot Lipase-Catalyzed Enantioselective Synthesis of (R)-(−)-N-Benzyl-3-(benzylamino)butanamide: The Effect of Solvent Polarity on Enantioselectivity Molecules lipase promiscuity aza-Michael addition stereoselectivity enantioselectivity chemoselectivity solvent engineering |
| title | One-Pot Lipase-Catalyzed Enantioselective Synthesis of (R)-(−)-N-Benzyl-3-(benzylamino)butanamide: The Effect of Solvent Polarity on Enantioselectivity |
| title_full | One-Pot Lipase-Catalyzed Enantioselective Synthesis of (R)-(−)-N-Benzyl-3-(benzylamino)butanamide: The Effect of Solvent Polarity on Enantioselectivity |
| title_fullStr | One-Pot Lipase-Catalyzed Enantioselective Synthesis of (R)-(−)-N-Benzyl-3-(benzylamino)butanamide: The Effect of Solvent Polarity on Enantioselectivity |
| title_full_unstemmed | One-Pot Lipase-Catalyzed Enantioselective Synthesis of (R)-(−)-N-Benzyl-3-(benzylamino)butanamide: The Effect of Solvent Polarity on Enantioselectivity |
| title_short | One-Pot Lipase-Catalyzed Enantioselective Synthesis of (R)-(−)-N-Benzyl-3-(benzylamino)butanamide: The Effect of Solvent Polarity on Enantioselectivity |
| title_sort | one pot lipase catalyzed enantioselective synthesis of r n benzyl 3 benzylamino butanamide the effect of solvent polarity on enantioselectivity |
| topic | lipase promiscuity aza-Michael addition stereoselectivity enantioselectivity chemoselectivity solvent engineering |
| url | https://www.mdpi.com/1420-3049/22/12/2189 |
| work_keys_str_mv | AT marinaaortegarojas onepotlipasecatalyzedenantioselectivesynthesisofrnbenzyl3benzylaminobutanamidetheeffectofsolventpolarityonenantioselectivity AT josedomingoriveraramirez onepotlipasecatalyzedenantioselectivesynthesisofrnbenzyl3benzylaminobutanamidetheeffectofsolventpolarityonenantioselectivity AT cgabrielaavilaortiz onepotlipasecatalyzedenantioselectivesynthesisofrnbenzyl3benzylaminobutanamidetheeffectofsolventpolarityonenantioselectivity AT eusebiojuaristi onepotlipasecatalyzedenantioselectivesynthesisofrnbenzyl3benzylaminobutanamidetheeffectofsolventpolarityonenantioselectivity AT fernandogonzalezmunoz onepotlipasecatalyzedenantioselectivesynthesisofrnbenzyl3benzylaminobutanamidetheeffectofsolventpolarityonenantioselectivity AT edmundocastillo onepotlipasecatalyzedenantioselectivesynthesisofrnbenzyl3benzylaminobutanamidetheeffectofsolventpolarityonenantioselectivity AT jaimeescalante onepotlipasecatalyzedenantioselectivesynthesisofrnbenzyl3benzylaminobutanamidetheeffectofsolventpolarityonenantioselectivity |