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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Autores principales: Bertello, L.E., Salto, M.L., De Lederkremer, R.M.
Formato: JOUR
Materias:
chimyl alcohol
fatty acid
article
esterification
nuclear magnetic resonance
reaction analysis
structure analysis
Catalysis
Esterification
Fatty Acids
Glycerides
Glyceryl Ethers
Kinetics
Lipase
Magnetic Resonance Spectroscopy
Molecular Structure
Pseudomonas
Solvents
Temperature
Acceso en línea:http://hdl.handle.net/20.500.12110/paper_00244201_v32_n8_p907_Bertello
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Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires
id todo:paper_00244201_v32_n8_p907_Bertello
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spelling todo:paper_00244201_v32_n8_p907_Bertello2023-10-03T14:35:12Z Lipase-catalyzed monoesterification of 1-O-Hexadecylglycerol in organic solvents Bertello, L.E. Salto, M.L. De Lederkremer, R.M. chimyl alcohol fatty acid article esterification nuclear magnetic resonance reaction analysis structure analysis Catalysis Esterification Fatty Acids Glycerides Glyceryl Ethers Kinetics Lipase Magnetic Resonance Spectroscopy Molecular Structure Pseudomonas Solvents Temperature 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. Fil:Bertello, L.E. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Salto, M.L. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:De Lederkremer, R.M. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_00244201_v32_n8_p907_Bertello
institution Universidad de Buenos Aires
institution_str I-28
repository_str R-134
collection Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic chimyl alcohol
fatty acid
article
esterification
nuclear magnetic resonance
reaction analysis
structure analysis
Catalysis
Esterification
Fatty Acids
Glycerides
Glyceryl Ethers
Kinetics
Lipase
Magnetic Resonance Spectroscopy
Molecular Structure
Pseudomonas
Solvents
Temperature
spellingShingle chimyl alcohol
fatty acid
article
esterification
nuclear magnetic resonance
reaction analysis
structure analysis
Catalysis
Esterification
Fatty Acids
Glycerides
Glyceryl Ethers
Kinetics
Lipase
Magnetic Resonance Spectroscopy
Molecular Structure
Pseudomonas
Solvents
Temperature
Bertello, L.E.
Salto, M.L.
De Lederkremer, R.M.
Lipase-catalyzed monoesterification of 1-O-Hexadecylglycerol in organic solvents
topic_facet chimyl alcohol
fatty acid
article
esterification
nuclear magnetic resonance
reaction analysis
structure analysis
Catalysis
Esterification
Fatty Acids
Glycerides
Glyceryl Ethers
Kinetics
Lipase
Magnetic Resonance Spectroscopy
Molecular Structure
Pseudomonas
Solvents
Temperature
description 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.
format JOUR
author Bertello, L.E.
Salto, M.L.
De Lederkremer, R.M.
author_facet Bertello, L.E.
Salto, M.L.
De Lederkremer, R.M.
author_sort Bertello, L.E.
title Lipase-catalyzed monoesterification of 1-O-Hexadecylglycerol in organic solvents
title_short Lipase-catalyzed monoesterification of 1-O-Hexadecylglycerol in organic solvents
title_full Lipase-catalyzed monoesterification of 1-O-Hexadecylglycerol in organic solvents
title_fullStr Lipase-catalyzed monoesterification of 1-O-Hexadecylglycerol in organic solvents
title_full_unstemmed Lipase-catalyzed monoesterification of 1-O-Hexadecylglycerol in organic solvents
title_sort lipase-catalyzed monoesterification of 1-o-hexadecylglycerol in organic solvents
url http://hdl.handle.net/20.500.12110/paper_00244201_v32_n8_p907_Bertello
work_keys_str_mv AT bertellole lipasecatalyzedmonoesterificationof1ohexadecylglycerolinorganicsolvents
AT saltoml lipasecatalyzedmonoesterificationof1ohexadecylglycerolinorganicsolvents
AT delederkremerrm lipasecatalyzedmonoesterificationof1ohexadecylglycerolinorganicsolvents
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