Lipase-catalyzed monoesterification of 1-O-Hexadecylglycerol in organic solvents
A simple method is presented to esterify 1-O-hexadecyl-rac-glycerol using lipases in different organic solvents. The following fatty acids were used: C(14:0), C(16:0), C(18:0), C(18:1), and C(18:2). Monoesterification was achieved by using a limiting amount of the fatty acid. Both the 1-O- hexadecyl...
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| Formato: | Capítulo de libro |
| Lenguaje: | Inglés |
| Publicado: |
1997
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| Acceso en línea: | Registro en Scopus DOI Handle Registro en la Biblioteca Digital |
| Aporte de: | Registro referencial: Solicitar el recurso aquí |
| LEADER | 08394caa a22008417a 4500 | ||
|---|---|---|---|
| 001 | PAPER-3221 | ||
| 003 | AR-BaUEN | ||
| 005 | 20230518203241.0 | ||
| 008 | 190411s1997 xx ||||fo|||| 00| 0 eng|d | ||
| 024 | 7 | |2 scopus |a 2-s2.0-0030750149 | |
| 024 | 7 | |2 cas |a 1-O-hexadecyl-2-O-hexadecanoylglycerol; 1-O-hexadecyl-3-O-hexadecanoylglycerol, 17810-56-9; chimyl alcohol, 53584-29-5; Fatty Acids; Glycerides; Glyceryl Ethers; Lipase, EC 3.1.1.3; Solvents | |
| 040 | |a Scopus |b spa |c AR-BaUEN |d AR-BaUEN | ||
| 030 | |a LPDSA | ||
| 100 | 1 | |a Bertello, L.E. | |
| 245 | 1 | 0 | |a Lipase-catalyzed monoesterification of 1-O-Hexadecylglycerol in organic solvents |
| 260 | |c 1997 | ||
| 270 | 1 | 0 | |m De Lederkremer, R.M.; Departamento de Quimica Organica, FCEN, Universidad de Buenos Aires, 1428 Buenos Aires, Argentina; email: lederk@quimor.qo.fcen.uba.ar |
| 506 | |2 openaire |e Política editorial | ||
| 504 | |a McConville, M.J., Ferguson, M.A.J., The Structure, Biosynthesis and Function of Glycosylated Phosphatidylinositols in the Parasitic Protozoa and Higher Eukaryotes (1993) Biochem. J., 294, pp. 305-324 | ||
| 504 | |a Lederkremer, R.M., Lima, C.E., Ramirez, M.I., Gonçalvez, M.F., Colli, W., Hexadecylpalmitoylglycerol or Ceramide Is Linked to Similar Glycophosphoinositol Anchor-Like Structures in Trypanosoma cruzi (1993) Eur. J. Biochem., 218, pp. 929-936 | ||
| 504 | |a Heise, N., Cardoso De Almeida, M.L., Ferguson, M.A.J., Characterization of the Lipid Moiety of the Glycosylphosphatidylinositol Anchor of Trypanosoma cruzi 1G7-antigen (1995) Molec. Biochem. Parasitol., 70, pp. 71-84 | ||
| 504 | |a Acosta Serrano, A., Schenkman, S., Yoshida, N., Mehlert, A., Richardson, J.M., Ferguson, M.A.J., The Lipid Structure of the Glycosylphosphatidylinositol-Anchored Mucin-Like Sialic Acid Acceptors of Trypanosoma cruzi. Changes during Parasitic Differentiation from Epimastigotes to Infective Metacyclic Trypomastigote Forms (1995) J. Biol. Chem., 270, pp. 27244-27253 | ||
| 504 | |a Bertello, L.E., Gonçalvez, M.F., Colli, W., Lederkremer, R.M., Structural Analysis of Inositol Phospholipids from Trypanosoma cruzi Epimastigote Forms (1995) Biochem. J., 310, pp. 255-261 | ||
| 504 | |a Uhrig, M.L., Couto, A.S., Colli, W., Lederkremer, R.M., Characterization of Inositol Phospholipids in Trypanosoma cruzi Trypomastigote Forms (1996) Biochim. Biophys. Acta, 1300, pp. 233-239 | ||
| 504 | |a Bornscheuer, U.T., Lipase-Catalyzed Syntheses of Monoacylglycerols (1995) Enzyme Microb. Technol., 17, pp. 578-586 | ||
| 504 | |a Kwon, S.J., Han, J.J., Rhee, J.S., Production and in situ Separation of Mono- or Diacylglycerol Catalyzed by Lipases in n-Hexane (1995) Enzyme Microb. Technol., 17, pp. 700-704 | ||
| 504 | |a Meusel, D., Weber, N., Mukherjee, K.D., Stereoselectivity of Lipases: Esterification Reactions of Octadecylglycerol (1992) Chem. Phys. Lipids, 61, pp. 193-198 | ||
| 504 | |a Haraldsson, G.G., Thorarensen, A., The Generation of Glyceryl Ether Lipids Highly Enriched with Eicosapentaenoic Acid and Docosahexaenoic Acid by Lipase (1994) Tetrahedron Lett., 35, pp. 7681-7684 | ||
| 504 | |a Virto, M.D., Agud, I., Montero, S., Blanco, A., Solozabal, R., Lascaray, J.M., Llama, M.J., De Renobales, M., Kinetic Properties of Soluble and Immobilized Candida rugosa Lipase (1995) Appl. Biochem. Biotechnol., 50, pp. 127-136 | ||
| 504 | |a Sjursnes, B.J., Anthonsen, T., Acyl Migration in 1,2-Dibutyrin. Dependence on Solvent and Water Activity (1994) Biocatalysis, 9, pp. 285-297 | ||
| 504 | |a Roberts, W.L., Myher, J.J., Kuksis, A., Rosenberry, T.L., Alkylacylglycerol Molecular Species in the Glycosylinositol Phospholipid Membrane Anchor of Bovine Erythrocyte Acetylcholinesterase (1988) Biochem. Biophys. Res. Commun., 150, pp. 271-277 | ||
| 504 | |a Gubicza, L., Szakács-Schmidt, A., Effects of the Reaction Conditions on the Enantioselective Esterification Using Candida cylindracea Lipase (1994) Biocatalysis, 9, pp. 131-143 | ||
| 504 | |a Miller, C., Austin, H., Posorske, L., Gonzalez, J., Characteristic of an Immobilized Lipase for the Commercial Synthesis of Esters (1988) J. Am. Oil Chem. Soc., 65, pp. 927-931 | ||
| 504 | |a Pastor, E., Otero, C., Ballesteros, A., Enzymatic Preparation of Mono- and Di-Stearin by Glycerolysis of Ethyl Stearate and Direct Esterification of Glycerol in the Presence of a Lipase from Candida antarctica (Novozym 435) (1995) Biocatal. Biotransform., 12, pp. 147-157 | ||
| 504 | |a Chaudhary, S.K., Hernandez, O., A Simplified Procedure for the Preparation of Triphenylmethylethers (1979) Tetrahedron Lett., 2, pp. 95-98 | ||
| 504 | |a Hassner, A., Alexanian, V., Direct Room Temperature Esterification of Carboxylic Acids (1978) Tetrahedron Lett., 46, pp. 4475-4478 | ||
| 504 | |a Ogawa, T., Horisaki, T., Synthesis of 2-O-Hexadecanoyl-1-O-Hexadecyl-[α-Glc-6SO 3Na-(1-6)-α-Glc-(1-6)-α-Glc-(1-3)]-sn-glycerol: A Proposed Structure for the Glyceroglucolipids of Human Gastric Secretion and of the Mucous Barrier of Rat-Stomach Antrum (1983) Carbohydr. Res., 123, pp. C1-C4 | ||
| 504 | |a Subrahmanyam, C., Venkateswara Rao, C., Anjaneyulu, V., Satyanarayana, P., Subba Rao, P.V., Ward, R.S., Pelter, A., New Diterpenes from a New Species of Lobophytum Soft Coral of the South Andaman Coast (1992) Tetrahedron, 48, pp. 3111-3120 | ||
| 520 | 3 | |a A simple method is presented to esterify 1-O-hexadecyl-rac-glycerol using lipases in different organic solvents. The following fatty acids were used: C(14:0), C(16:0), C(18:0), C(18:1), and C(18:2). Monoesterification was achieved by using a limiting amount of the fatty acid. Both the 1-O- hexadecyl-3-O-acylglycerol and the 2-O-acylglycerol were obtained in a total yield of 75% and a ratio of 7:1 in dichloromethane after 3 d. Chromatographic data for the monoesters, useful for the identification of the natural products, are given (gas-liquid chromatography, thin-layer chromatography, reverse-phase thin-layer chromatography). The structure was confirmed by a chemical synthesis of 1-O-hexadecyl-2-O-hexadecanoylglycerol. The 3-O- glyceride was also formed by acyl migration, as the minor component. The monoesters were separated by column chromatography and characterized by 1H and 13C nuclear magnetic resonance spectra. |l eng | |
| 536 | |a Detalles de la financiación: Consejo Nacional de Investigaciones Científicas y Técnicas | ||
| 536 | |a Detalles de la financiación: Universidad de Buenos Aires | ||
| 536 | |a Detalles de la financiación: This investigation received financial support from UNDP/World Bank/World Health Organization Special Programme for Research and Training in Tropical Diseases, Consejo Nacional de Investiga-ciones Científicas y Técnicas (CONICET) and Universidad de Buenos Aires. | ||
| 593 | |a CIHIDECAR, Depto. de Quim. Orgánica, Universidad de Buenos Aires, Buenos Aires, Argentina | ||
| 593 | |a Depto. de Quim. Orgánica, Fac. de Ciencias Exactas y Naturales, Universidad de Buenos Aires, 1428, Buenos Aires, Argentina | ||
| 690 | 1 | 0 | |a CHIMYL ALCOHOL |
| 690 | 1 | 0 | |a FATTY ACID |
| 690 | 1 | 0 | |a ARTICLE |
| 690 | 1 | 0 | |a ESTERIFICATION |
| 690 | 1 | 0 | |a NUCLEAR MAGNETIC RESONANCE |
| 690 | 1 | 0 | |a REACTION ANALYSIS |
| 690 | 1 | 0 | |a STRUCTURE ANALYSIS |
| 690 | 1 | 0 | |a CATALYSIS |
| 690 | 1 | 0 | |a ESTERIFICATION |
| 690 | 1 | 0 | |a FATTY ACIDS |
| 690 | 1 | 0 | |a GLYCERIDES |
| 690 | 1 | 0 | |a GLYCERYL ETHERS |
| 690 | 1 | 0 | |a KINETICS |
| 690 | 1 | 0 | |a LIPASE |
| 690 | 1 | 0 | |a MAGNETIC RESONANCE SPECTROSCOPY |
| 690 | 1 | 0 | |a MOLECULAR STRUCTURE |
| 690 | 1 | 0 | |a PSEUDOMONAS |
| 690 | 1 | 0 | |a SOLVENTS |
| 690 | 1 | 0 | |a TEMPERATURE |
| 700 | 1 | |a Salto, M.L. | |
| 700 | 1 | |a De Lederkremer, R.M. | |
| 773 | 0 | |d 1997 |g v. 32 |h pp. 907-911 |k n. 8 |p LIPIDS |x 00244201 |w (AR-BaUEN)CENRE-2318 |t Lipids | |
| 856 | 4 | 1 | |u https://www.scopus.com/inward/record.uri?eid=2-s2.0-0030750149&doi=10.1007%2fs11745-997-0117-x&partnerID=40&md5=c45d5a516f8a390a66f1cc1f6b53fa3e |y Registro en Scopus |
| 856 | 4 | 0 | |u https://doi.org/10.1007/s11745-997-0117-x |y DOI |
| 856 | 4 | 0 | |u https://hdl.handle.net/20.500.12110/paper_00244201_v32_n8_p907_Bertello |y Handle |
| 856 | 4 | 0 | |u https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00244201_v32_n8_p907_Bertello |y Registro en la Biblioteca Digital |
| 961 | |a paper_00244201_v32_n8_p907_Bertello |b paper |c PE | ||
| 962 | |a info:eu-repo/semantics/article |a info:ar-repo/semantics/artículo |b info:eu-repo/semantics/publishedVersion | ||
| 999 | |c 64174 | ||