Characterization of fatty amides produced by lipase-catalyzed amidation of multi-hydroxylated fatty acids

Levinson, William E.; Kuo, Tsung Min; Knothe, Gerhard

doi:10.1016/j.biortech.2007.04.058

Cited by 13 publications

(7 citation statements)

References 10 publications

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“…Fatty amides were previously found in freshwater green algae. 44 In the present work, m/z 59 and 72 were observed in Chlamy's USP (TLC fraction 5, Figure 3), which are the characteristic amide peaks resulting from McLaffery rearrangement of γ-cleavage, 45 indicating the presence of a trace of fatty amide in Chlamy.…”

Section: 39mentioning

confidence: 95%

Microalgae Lipid Characterization

Yao

Gerde

Lee

et al. 2015

J. Agric. Food Chem.

171

132

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To meet the growing interest of utilizing microalgae biomass in the production of biofuels and nutraceutical and pharmaceutical lipids, we need suitable analytical methods and a comprehensive database for their lipid components. The objective of the present work was to demonstrate methodology and provide data on fatty acid composition, lipid class content and composition, characteristics of the unsaponifiables, and type of chlorophylls of five microalgae. Microalgae lipids were fractionated into TAG, FFA, and polar lipids using TLC, and the composition of fatty acids in total lipids and in each lipid class, hydrocarbons, and sterols were determined by GC-MS. Glyco-and phospholipids were profiled by LC/ESI-MS. Chlorophylls and their related metabolites were qualified by LC/APCI-MS. The melting and crystallization profiles of microalgae total lipids and their esters were analyzed by DSC to evaluate their potential biofuel applications. Significant differences and complexities of lipid composition among the algae tested were observed. The compositional information is valuable for strain selection, downstream biomass fractionation, and utilization. ABSTRACT: To meet the growing interest of utilizing microalgae biomass in the production of biofuels and nutraceutical and pharmaceutical lipids, we need suitable analytical methods and a comprehensive database for their lipid components. The objective of the present work was to demonstrate methodology and provide data on fatty acid composition, lipid class content and composition, characteristics of the unsaponifiables, and type of chlorophylls of five microalgae. Microalgae lipids were fractionated into TAG, FFA, and polar lipids using TLC, and the composition of fatty acids in total lipids and in each lipid class, hydrocarbons, and sterols were determined by GC-MS. Glyco-and phospholipids were profiled by LC/ESI-MS. Chlorophylls and their related metabolites were qualified by LC/APCI-MS. The melting and crystallization profiles of microalgae total lipids and their esters were analyzed by DSC to evaluate their potential biofuel applications. Significant differences and complexities of lipid composition among the algae tested were observed. The compositional information is valuable for strain selection, downstream biomass fractionation, and utilization.

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Section: 39mentioning

confidence: 95%

Microalgae Lipid Characterization

Yao

Gerde

Lee

et al. 2015

J. Agric. Food Chem.

171

132

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“…23 Furthermore, it was shown that multi-hydroxylated fatty acids were efficiently converted into the corresponding amides employing the same method. 24 enzyme to 1 mmol substrate. 25 In addition to the enzymatic methods above, the microorganisms Bacillus cereus, 26,27 Streptomyces halstedii, 28 and Bacillus subtilis 29 have been used to form primary amides 5 from carboxylic acids.…”

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confidence: 99%

Catalytic amide formation from non-activated carboxylic acids and amines

et al. 2014

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The amide functionality is found in a wide variety of biological and synthetic structures such as proteins, polymers, pesticides and pharmaceuticals. Due to the fact that synthetic amides are still mainly produced by the aid of coupling reagents with poor atom-economy, the direct catalytic formation of amides from carboxylic acids and amines has become a field of emerging importance. A general, efficient and selective catalytic method for this transformation would meet well with the increasing criterias for green 10 chemistry. This review covers catalytic and synthetically relevant methods for direct condensation of carboxylic acids and amines. A comprehensive overview of homogeneous and heterogeneous catalytic methods is presented, covering biocatalysis, Lewis acid catalysts based on boron and metals as well an assortment of other types of catalysts.

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“…Amidas graxas biologicamente ativas, palmitoiletanolamida (1), anandamida (2), cis-oleamida (3), oleiletanolamida (4) e N-benzil-Ztetracosenamida (5) Os ácidos graxos 6a-c (Esquema 1) foram esterificados utilizando-se H 2 SO 4 e metanol a temperatura de 65 o C por 4 h, formando os respectivos ésteres metílicos graxos 7a-c.…”

Section: 46unclassified

“…[1][2][3][4][5][6] Esta classe de compostos tem sido naturalmente encontrada em vegetais terrestres e aquáticos, em animais e micro-organismos. No reino vegetal, estão presentes nas algas Rizoclonium hierogliphicun, Zoostera marina e Sebastes mentella, nos vegetais Lepidium meyenii (maca) e Zanthoxylum sp.…”

Section: Introductionunclassified

Síntese de novas amidas graxas a partir da aminólise de ésteres metílicos

et al. 2010

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. Itália km 08 s/n, 96203-000 Rio Grande -RS, Brasil Recebido em 11/11/09; aceito em 17/2/10; publicado na web em 21/5/10 SYNTHESIS OF NEW FATTY ACIDS AMIDES FROM AMINOLYSIS OF FAMES. Recent biochemical and pharmacological studies have led to the characterization of different fatty acid amides as a new family of biologically active lipids. Here, we describe the synthesis of new amides from C16:0, 18:0, 18:1 and 18:1, OH fatty acids (FFA) families with cyclic and acyclic amines and demonstrate for the first time that these compounds produce citotoxic effects. Application of this method to the synthesis of fatty acid amides was performed using the esters aminolysis as a key step and various carboxylic amides were prepared in good yield from fatty acid methyl esters (FAMEs).

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Characterization of fatty amides produced by lipase-catalyzed amidation of multi-hydroxylated fatty acids

Cited by 13 publications

References 10 publications

Microalgae Lipid Characterization

Microalgae Lipid Characterization

Catalytic amide formation from non-activated carboxylic acids and amines

Síntese de novas amidas graxas a partir da aminólise de ésteres metílicos

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