Enzymatically prepared n-alkyl esters of glucuronic acid: The effect of freeze-drying conditions and hydrophobic chain length on thermal behavior

Blecker, Christophe; Danthine, Sabine; Petre, Maguy; Lognay, Georges; Moreau, Benoît; Elst, Luce Vander; Paquot, Michel; Deroanne, Claude

doi:10.1016/j.jcis.2008.02.002

Cited by 8 publications

(2 citation statements)

References 16 publications

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“…In previous papers, we have already described the enzymatic synthesis and surface properties of glucuronate fatty esters [6][7][8][9][10]. The effect of the hydrophobic chain length on the surface properties of these molecules was examined.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Surface‐Active Properties of Uronic Amide Derivatives, Surfactants from Renewable Organic Raw Materials

Praly

Razafindralambo

Wathelet

et al. 2010

J Surfact & Detergents

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Short chemical syntheses were developed to produce a new set of surfactants from uronic acids derived from widely available raw materials. Three different strategies were used to synthesize uronic amide derivatives, the structures of which were totally characterized by spectrometric methods (IR, MS, 1 H-RMN and 13 C-RMN). The best one, using an acid chloride as the synthetic intermediate, furnished the expected amides as a mixture of anomers in 46-58% global yield. Surface-active properties (CMC, c cmc , C max , A min ) of homologous series of uronic acid N-alkylamides from C8 to C18 were also assessed. In general, these sugar-based surfactants exhibited good surface-activities, and appeared as valuable nonionic surfactants compared to octylphenol 9-10 ethylene oxide condensate, the most well-known nonionic surfactant. Increasing the alkyl chain length influenced the CMC values for both glucuronic and galacturonic N-alkylamide derivatives. The galacturonic N-alkylamides decreased c cmc at slower values than their counterpart's glucuronic N-alkylamides. AbbreviationsCOSY Correlation spectroscopy DCC Dicyclohexyl carbodiimide DMF Dimethyl formamide DMSO Dimethyl sulfoxide ESIMS Electrospray ionisation mass spectrometry HMBC Heteronuclear multiple bond correlation HSQC Heteronuclear single quantum correlation NOESY Nuclear Overhauser effect spectroscopy TLC Thin layer chromatography TMS Tetramethylsilane

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Section: Introductionmentioning

confidence: 99%

Synthesis and Surface‐Active Properties of Uronic Amide Derivatives, Surfactants from Renewable Organic Raw Materials

Praly

Razafindralambo

Wathelet

et al. 2010

J Surfact & Detergents

View full text Add to dashboard Cite

show abstract

“…The classical chemical method of synthesis of these esters faces several major drawbacks. The conventional approach using chemical catalysts requires high temperature which causes product coloration, high energy consumption and the recovery of considerable amount of side products [2]. However, the use of biological catalysts has a great potential for synthesis due to the direct use of unmodified substrates, mild reaction conditions, low energy requirement and high regioselectivity of the biocatalyst [3].…”

Section: Introductionmentioning

confidence: 99%

High Performance Enzyme-Catalyzed Synthesis and Characterization of a Nonionic Surfactant

Adnani¹

2013

IOSR-JAC

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Parameters Influencing Lipase-Catalyzed Glycolipid Synthesis by (Trans-)Esterification Reaction

Hollenbach

Ochsenreither

Syldatk

2021

Advances in Biochemical Engineering/Biotechnology

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Enzymatically prepared n-alkyl esters of glucuronic acid: The effect of freeze-drying conditions and hydrophobic chain length on thermal behavior

Cited by 8 publications

References 16 publications

Synthesis and Surface‐Active Properties of Uronic Amide Derivatives, Surfactants from Renewable Organic Raw Materials

Synthesis and Surface‐Active Properties of Uronic Amide Derivatives, Surfactants from Renewable Organic Raw Materials

High Performance Enzyme-Catalyzed Synthesis and Characterization of a Nonionic Surfactant

Parameters Influencing Lipase-Catalyzed Glycolipid Synthesis by (Trans-)Esterification Reaction

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