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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Sumario: | 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. |
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Bibliografía: | Akiyama, K., Kawamoto, S., Fujimoto, H., Ishibashi, M., Absolute stereochemistry of TT-1 (rasfonin), an α-pyrone-containing natural product from a fungus, Trichurus terrophilus (2003) Tetrahedron Letters, 44 (46), pp. 8427-8431. , DOI 10.1016/j.tetlet.2003.09.136 Bommarius, A.S., Riebel, B.R., (2004) Biocatalysis, Fundamentals and Applications, , Weinheim: Wiley-VCH Buchholz, K., Kasche, V., Bornscheuer, U.T., (2005) Biocatalysis and Enzyme Technology, , Weinheim: Wiley-VCH Carrea, G., Riva, S., (2008) Organic Synthesis with Enzymes in Nonaqueous Media, , Weinheim: Wiley-VCH Carrea, G., De Amici, M., De Micheli, C., Liverani, P., Carnielli, M., Riva, S., Nitrile oxides in medicinal chemistry. 5. Lipase PS-catalyzed resolution of a set of heterocyclic derivatives (1993) Tetrahedron Asymmetry, 4 (5), pp. 1063-1072. , DOI 10.1016/S0957-4166(00)80155-X Czuba, I.R., Zammit, S., Rizzacasa, M.A., Total synthesis of the marine sponge metabolites ( - )-rottnestol, ( - lol B (2003) Org Biomol Chem, 1, pp. 2044-2056 Faber, K., (2000) Biotransformations in Organic Chemistry: A Textbook, , Berlin: Springer Fadnavis, N.W., Sharfuddin, M., Vadivel, S.K., Resolution of racemic 2-amino-1-butanol with immobilised penicillin G acylase (1999) Tetrahedron Asymmetry, 10 (23), pp. 4495-4500. , PII S0957416699005315 Forró, E., Fülöp, F., A new enzymatic strategy for the preparation of (2 R ,3 S )-3-phenylisoserine: A key intermediate for the Taxol side chain (2010) Tetrahedron Asymm, 21, pp. 637-639 Francalanci, F., Cesti, P., Cabri, W., Bianchi, D., Martinengo, T., Foà, M., Lipase-catalyzed resolution of chiral 2-amino 1-alcohols (1987) J Org Chem, 52, pp. 5079-5082 Galman, J.L., Hailes, H.C., Application of a modifi ed Mosher 's method for the determination of enantiomeric ratio and absolute confi guration at C-3 of chiral 1,3-dihydroxy ketones (2009) Tetrahedron Asymm, 20, pp. 1828-1831 Gonzalez-Sabin, J., Gotor, V., Rebolledo, F., Enantioselective acylation of rac-2-phenylcycloalkanamines catalyzed by lipases (2005) Tetrahedron Asymmetry, 16 (18), pp. 3070-3076. , DOI 10.1016/j.tetasy.2005.07.033, PII S095741660500594X Gotor, V., Alfonso, I., García-Urdiales, E., (2007) Asymmetric Organic Synthesis with Enzymes, , Weinheim: Wiley-VCH Juhl, P.B., Trodler, P., Tyagi, S., Pleiss, J., Modeling substrate specifi city and enantioselectivity for lipases and esterases by substrate-imprinted docking (2009) BMC Struct Biol, 9, pp. 39-45 Kazlauskas, R.J., Weissfloch, A.N.E., Rappaport, A.T.A., Cuccia, L.A., A rule to predict which enantiomer of a secondary alcohol reacts faster in reactions catalyzed by cholesterol esterase, lipase from Pseudomonas cepacia , and lipase from Candida rugosa (1991) J Org Chem, 56, pp. 2656-2665 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 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 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 Nyerges, M., Bendell, D., Arany, A., Hibbs, D.E., Coles, S.J., Hursthouse, M.B., Groundwater, P.W., Meth-Cohn, O., Silver acetate-catalysed asymmetric 1,3-dipolar cycloadditions of imines and chiral acrylamides (2005) Tetrahedron, 61 (15), pp. 3745-3753. , DOI 10.1016/j.tet.2005.02.009 Pehk, T., Lippmaa, E., Lopp, M., Paju, A., Borer, B.C., Taylor, R.J.K., Determination of the absolute configuration of chiral secondary alcohols; new advances using 13C- and 2D-NMR spectroscopy (1993) Tetrahedron Asymmetry, 4 (7), pp. 1527-1532. , DOI 10.1016/S0957-4166(00)80354-7 Puertas, S., Brieva, R., Rebolledo, F., Gotor, V., Aminomethylation of chiral silyl enol ethers: Access toβ2 -homo tryptophane andβ2 -homolysine derivatives (1993) Tetrahedron, 49, pp. 4007-4014 Quintana, P.G., Baldessari, A., Lipase-catalyzed regioselective preparation of fatty acid esters of hydrocortisone (2009) Steroids, 74, pp. 1007-1014 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 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 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 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 Tobis, J., Thoman, Y., Tiller, J.C., Synthesis and characterization of chiral and thermo responsive amphiphilic co networks (2010) Polymer, 51, pp. 35-45 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 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 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 |
ISSN: | 10242422 |
DOI: | 10.3109/10242422.2011.578212 |