Abstract:
A series of novel fatty acid derivatives of pyridoxine, one of the three members of the vitamin B6 group, has been prepared. These products were obtained using an enzymatic approach. Several lipases catalyzed esterification and transesterification reactions of pyridoxine with carboxylic acid or alkyl carboxylates showed a remarkable regioselective behavior; only monoacyl derivatives were obtained. The surfactant activity, composition and clean enzymatic methodology applied in the preparation of these products make them useful as ingredients in cosmetic and pharmaceutical formulations or food additives.
Registro:
Documento: |
Artículo
|
Título: | Enzyme-catalyzed preparation of novel fatty acid derivatives of pyridoxine with surfactant activity |
Autor: | Baldessari, A.; Mangone, C.P. |
Filiación: | Departamento de Quimica Organica, Fac. de Ciencias Exactas y Naturales, Universidad de Buenos Aires, 1428 Buenos Aires, Argentina
|
Palabras clave: | Enzyme-catalyzed; Fatty acids; Pyridoxine; Surfactants; Biosynthesis; Carboxylic acids; Derivatives; Drug products; Enzymes; Esterification; Fatty acids; Food additives; Surface active agents; Vitamins; Regioselective; Nitrogen compounds; (5 hydroxy 4 hydroxymethyl 6 methylpyridin 3 yl)methyl 13 docosenoic acid; (5 hydroxy 4 hydroxymethyl 6 methylpyridin 3 yl)methyl 5,8,11,14 eicosatetraenoic acid; (5 hydroxy 4 hydroxymethyl 6 methylpyridin 3 yl)methyl 9 octadecanoic acid; (5 hydroxy 4 hydroxymethyl 6 methylpyridin 3 yl)methyl 9,12 octadecanoic acid; (5 hydroxy 4 hydroxymethyl 6 methylpyridin 3 yl)methyl 9,12,15 octadecatrienoic acid; (5 hydroxy 4 hydroxymethyl 6 methylpyridin 3 yl)methyleicosanoic acid; (5 hydroxy 4 hydroxymethyl 6 methylpyridin 3 yl)methyloctadecanoic acid; carboxylic acid; fatty acid derivative; food additive; pyridoxine derivative; surfactant; triacylglycerol lipase; unclassified drug; acylation; article; catalysis; cosmetic industry; drug activity; drug formulation; drug synthesis; enzymatic assay; enzyme substrate; nonhuman; pancreas; pharmaceutical engineering; swine; Sus scrofa |
Año: | 2002
|
Volumen: | 20
|
Número: | 4
|
Página de inicio: | 275
|
Página de fin: | 279
|
DOI: |
http://dx.doi.org/10.1080/10242420290004910 |
Título revista: | Biocatalysis and Biotransformation
|
Título revista abreviado: | Biocatal. Biotransform.
|
ISSN: | 10242422
|
CODEN: | BOBOE
|
Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_10242422_v20_n4_p275_Baldessari |
Referencias:
- Angerer, P., Von Schacky, C., ω-3 Polyunsaturated fatty acids and the cardiovascular system (2000) Curr. Opin. Lipidol., 11, pp. 57-63
- Baldessari, A., Mangone, C.P., (2000) Patent Pending, INPI, AR 00 01 04147
- Baldessari, A., Mangone, C.P., Gros, E.G., Lipase-catalyzed acylation and deacylation reactions of pyridoxine, member of vitamin B6 group (1998) Helv. Chim. Acta, 81, pp. 2407-2413
- Becher, P., (1966) Emulsions: Theory and Practice, , (Marcel Dekker, New York)
- Bowen, W.H., Food components and caries (1994) Adv. Dent. Res., 8, pp. 215-220
- Brown, L., Johnston, A., Sukling, C.J., Halling, P.J., Valivety, R.H., Pyridoxal derivatives as probes for water concentration in non-aqueous solvents (1993) J. Chem. Soc. Perkin Trans., 1, pp. 2777-2780
- (1997) Physical Properties! Pro™, Computational Chemistry Program, , revision (1997) (Fairfield, California)
- Driskell, J.A., Vitamin B6 requirements of humans (1994) Nutr. Res., 14, pp. 293-324
- Faber, K., (2000) Biotransformations in Organic Chemistry, A Textbook, 4th Ed, , (Springer, Berlin)
- Griffin, W.C., Classification of surface-active agents by HLB (1949) J. Soc. Cosmet. Chem., 1, pp. 311-316
- Korytnyk, W., Paul, B., Acyl migration and selective esterification in pyridoxol (1967) J. Org. Chem., 32, pp. 3791-3796
- Simopoulos, A.P., New products from the agri-food industry: The return of ω-3 fatty acids into the food supply (1999) Lipids, 34 (SUPPL.), pp. S297-S301
- Snider, B., Dietman, D.F., Pyridoxine therapy for acne flare (1974) Arch. Dermatol., 110, pp. 130-131
- Wong, C.H., Whitesides, G.M., Enzymes in synthetic organic chemistry (1994) Tetrahedron Organic Chemistry Series, 12. , In: Baldwin, J.E. and Magnus, P.D., eds; (Elsevier Science, Oxford)
- Wyatt, K.M., Efficacy of vitamin B6 in the treatment of premenstrual syndrome: Systematic review (1999) Br. Med. J., 318, pp. 1375-1381
Citas:
---------- APA ----------
Baldessari, A. & Mangone, C.P.
(2002)
. Enzyme-catalyzed preparation of novel fatty acid derivatives of pyridoxine with surfactant activity. Biocatalysis and Biotransformation, 20(4), 275-279.
http://dx.doi.org/10.1080/10242420290004910---------- CHICAGO ----------
Baldessari, A., Mangone, C.P.
"Enzyme-catalyzed preparation of novel fatty acid derivatives of pyridoxine with surfactant activity"
. Biocatalysis and Biotransformation 20, no. 4
(2002) : 275-279.
http://dx.doi.org/10.1080/10242420290004910---------- MLA ----------
Baldessari, A., Mangone, C.P.
"Enzyme-catalyzed preparation of novel fatty acid derivatives of pyridoxine with surfactant activity"
. Biocatalysis and Biotransformation, vol. 20, no. 4, 2002, pp. 275-279.
http://dx.doi.org/10.1080/10242420290004910---------- VANCOUVER ----------
Baldessari, A., Mangone, C.P. Enzyme-catalyzed preparation of novel fatty acid derivatives of pyridoxine with surfactant activity. Biocatal. Biotransform. 2002;20(4):275-279.
http://dx.doi.org/10.1080/10242420290004910