Biocatalytic synthesis of chiral N-(2-hydroxyalkyl)-acrylamides
The preparation of a series of novel chiral N-(2-hydroxylalkyl)-acrylamides through a lipase-catalyzed resolution of racemic alkanolamines is described. The absolute stereochemistry and enantiomeric excess of the products were determined by a modified Mosher's method. The method was validated f...
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Informa Healthcare
2011
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| Acceso en línea: | Registro en Scopus DOI Handle Registro en la Biblioteca Digital |
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| LEADER | 10618caa a22011657a 4500 | ||
|---|---|---|---|
| 001 | PAPER-23749 | ||
| 003 | AR-BaUEN | ||
| 005 | 20230518205529.0 | ||
| 008 | 190411s2011 xx ||||fo|||| 00| 0 eng|d | ||
| 024 | 7 | |2 scopus |a 2-s2.0-79957469963 | |
| 024 | 7 | |2 cas |a triacylglycerol lipase, 9001-62-1 | |
| 040 | |a Scopus |b spa |c AR-BaUEN |d AR-BaUEN | ||
| 030 | |a BOBOE | ||
| 100 | 1 | |a Monsalve, L.N. | |
| 245 | 1 | 0 | |a Biocatalytic synthesis of chiral N-(2-hydroxyalkyl)-acrylamides |
| 260 | |b Informa Healthcare |c 2011 | ||
| 270 | 1 | 0 | |m Baldessari, A.; Laboratorio de Biocatálisis, Departamento de Química Orgánica y UMYMFOR, Ciudad Universitaria, Pabellán 2, Piso 3, C1428EGA, Buenos Aires, Argentina; email: alib@qo.fcen.uba.ar |
| 506 | |2 openaire |e Política editorial | ||
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| 504 | |a Monsalve, L.N., MacHado Rada, M.Y., Ghini, A.A., Baldessari, A., An efficient enzymatic preparation of 20-pregnane succinates: Chemoenzymatic synthesis of 20β-hemisuccinyloxy- 5αH-pregnan-3-one (2008) Tetrahedron, 64, pp. 1721-1730 | ||
| 504 | |a Monsalve, L.N., Rosselli, S., Bruno, M., Baldessari, A., Lipasecatalysed preparation of acyl derivatives of the germacranolide cnicin (2009) J Mol Catal B: Enzym, 57, pp. 40-47 | ||
| 504 | |a Monsalve, L.N., Fatema, M.K., Nonami, H., Erra-Balsells, R., Baldessari, A., Lipase-catalyzed synthesis and characterization of a novel linear polyamidoamine oligomer (2010) Polymer, 51, pp. 2998-3005 | ||
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| 504 | |a Quintana, P.G., Baldessari, A., Lipase-catalyzed regioselective preparation of fatty acid esters of hydrocortisone (2009) Steroids, 74, pp. 1007-1014 | ||
| 504 | |a Rustoy, E.M., Baldessari, A., An efficient chemoenzymatic synthesis of the bactericide lapyrium chloride (2005) European Journal of Organic Chemistry, (21), pp. 4628-4632. , DOI 10.1002/ejoc.200500388 | ||
| 504 | |a Rustoy, E.M., Baldessari, A., Chemoselective enzymatic preparation of N-hydroxyalkylacrylamides, monomers for hydrophilic polymer matrices (2006) Journal of Molecular Catalysis B: Enzymatic, 39 (1-4), pp. 50-54. , DOI 10.1016/j.molcatb.2006.01.026, PII S1381117706000488 | ||
| 504 | |a Rustoy, E.M., Sato, Y., Nonami, H., Erra-Balsells, R., Baldessari, A., Lipase-catalyzed synthesis and characterization of copolymers from ethyl acrylate as the only monomer starting material (2007) Polymer, 48 (6), pp. 1517-1525. , DOI 10.1016/j.polymer.2007.01.040, PII S0032386107000791 | ||
| 504 | |a Tian, Y., Lu, W., Che, Y., Shen, L.B., Jiang, L.M., Shen, Z.Q., Synthesis and characterization of macroporous silica modifi ed with optically active poly[ N -(oxazolinylphenyl)acrylamide] derivatives for potential application as chiral stationary phases (2010) J Appl Polym Sci, 115, pp. 999-1007 | ||
| 504 | |a Tobis, J., Thoman, Y., Tiller, J.C., Synthesis and characterization of chiral and thermo responsive amphiphilic co networks (2010) Polymer, 51, pp. 35-45 | ||
| 504 | |a Torre, O., Gotor-Fernandez, V., Alfonso, I., Garcia-Alles, L.F., Gotor, V., Study of the chemoselectivity in the aminolysis reaction of methyl acrylate catalysed by lipase B from Candida antarctica (2005) Advanced Synthesis and Catalysis, 347 (7-8), pp. 1007-1014. , DOI 10.1002/adsc.200505025 | ||
| 504 | |a Turcu, M.C., Perkiöp, Kanerva, L.T., Chemoen zymatic method for the preparation of γ-amino alcohols from phenylfuran- based aldehydes; Lipase-catalyzed kinetic resolution of β-hydroxy nitriles (2010) Tetrahedron Asymm, 21, pp. 739-745 | ||
| 504 | |a Xia, X., Wang, Y.H., Yang, B., Wang, X., Wheat germ lipase catalyzed kinetic resolution of secondary alcohols in non-aqueous media (2009) Biotechnol Lett., 31, pp. 83-87 | ||
| 520 | 3 | |a The preparation of a series of novel chiral N-(2-hydroxylalkyl)-acrylamides through a lipase-catalyzed resolution of racemic alkanolamines is described. The absolute stereochemistry and enantiomeric excess of the products were determined by a modified Mosher's method. The method was validated for this particular case by the synthesis of an enantiomerically pure product. Moreover, the stereoselective behavior of the lipase in this reaction is discussed. © 2011 Informa UK, Ltd. |l eng | |
| 536 | |a Detalles de la financiación: PICT 2005-32735 | ||
| 536 | |a Detalles de la financiación: PIP 112-200801-00801/09 | ||
| 536 | |a Detalles de la financiación: CONICET PIP 112-200801-00801/09 and ANPCyT PICT 2005-32735 for partial financial support. The authors report no conflicts of interest. The authors alone are responsible for the content and writing of the paper. | ||
| 593 | |a Laboratorio de Biocatálisis, Departamento de Química Orgánica y UMYMFOR, Ciudad Universitaria, Pabellán 2, Piso 3, C1428EGA, Buenos Aires, Argentina | ||
| 690 | 1 | 0 | |a CANDIDA ANTARCTICA LIPASE B |
| 690 | 1 | 0 | |a MOSHER' S METHOD |
| 690 | 1 | 0 | |a N-(HYDROXYALKYL)-ACRYLAMIDES |
| 690 | 1 | 0 | |a PRIMARY ALCOHOL |
| 690 | 1 | 0 | |a STEREOSELECTIVITY |
| 690 | 1 | 0 | |a ENANTIOMERS |
| 690 | 1 | 0 | |a ABSOLUTE STEREOCHEMISTRY |
| 690 | 1 | 0 | |a ACRYLAMIDES |
| 690 | 1 | 0 | |a BIOCATALYTIC SYNTHESIS |
| 690 | 1 | 0 | |a CANDIDA ANTARCTICA LIPASE B |
| 690 | 1 | 0 | |a ENANTIOMERIC EXCESS |
| 690 | 1 | 0 | |a LIPASE-CATALYZED RESOLUTION |
| 690 | 1 | 0 | |a MOSHER' S METHOD |
| 690 | 1 | 0 | |a PRIMARY ALCOHOLS |
| 690 | 1 | 0 | |a STEREOSELECTIVITY |
| 690 | 1 | 0 | |a ACRYLAMIDE DERIVATIVE |
| 690 | 1 | 0 | |a ALKANOLAMINE |
| 690 | 1 | 0 | |a TRIACYLGLYCEROL LIPASE |
| 690 | 1 | 0 | |a AMINOLYSIS |
| 690 | 1 | 0 | |a ARTICLE |
| 690 | 1 | 0 | |a BIOCATALYSIS |
| 690 | 1 | 0 | |a CANDIDA ANTARCTICA |
| 690 | 1 | 0 | |a CATALYST |
| 690 | 1 | 0 | |a CHEMICAL REACTION |
| 690 | 1 | 0 | |a CHIRALITY |
| 690 | 1 | 0 | |a ENANTIOMER |
| 690 | 1 | 0 | |a ENANTIOSELECTIVITY |
| 690 | 1 | 0 | |a ENZYME MECHANISM |
| 690 | 1 | 0 | |a ENZYME SPECIFICITY |
| 690 | 1 | 0 | |a MOSHER METHOD |
| 690 | 1 | 0 | |a NONHUMAN |
| 690 | 1 | 0 | |a RELIABILITY |
| 690 | 1 | 0 | |a STEREOCHEMISTRY |
| 690 | 1 | 0 | |a STRUCTURE ANALYSIS |
| 690 | 1 | 0 | |a SYNTHESIS |
| 690 | 1 | 0 | |a TECHNIQUE |
| 690 | 1 | 0 | |a CANDIDA ANTARCTICA |
| 700 | 1 | |a Rustoy, E.M. | |
| 700 | 1 | |a Baldessari, A. | |
| 773 | 0 | |d Informa Healthcare, 2011 |g v. 29 |h pp. 87-95 |k n. 2-3 |p Biocatal. Biotransform. |x 10242422 |w (AR-BaUEN)CENRE-3908 |t Biocatalysis and Biotransformation | |
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