Synthesis of novel d-glucuronic acid fatty esters using Candida antarctica lipase in tert-butanol

Moreau, Benoît; Lognay, Georges; Blecker, Christophe; Brohée, Jean-Christophe; Chéry, Florence; Rollin, Patrick; Paquot, Michel; Marlier, M.

doi:10.1023/b:bile.0000018262.57902.68

Cited by 21 publications

(16 citation statements)

References 9 publications

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“…As GEs enable selective cleavage of alkali-labile bonds at acidic pH values, GEs would also allow biomass degradation at a lower pH where other alkali-labile structures can be retained. In addition, production of alkyl-branched glucuronic acid derivatives using the synthetic capabilities of GEs could yield bioactive compounds such as nonionic surfactants for cosmetic and pharmaceutical applications (Moreau et al 2004) and improved prodrugs against tumours (de Graaf et al 2004). To support such developments, substantial effort is required to broaden our knowledge about GEs and their hydrolytic and synthetic potentials.…”

Section: Introductionmentioning

confidence: 99%

Characterisation of three fungal glucuronoyl esterases on glucuronic acid ester model compounds

Hüttner

Klaubauf

Vries

et al. 2017

Appl Microbiol Biotechnol

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The glucuronoyl esterases (GEs) that have been identified so far belong to family 15 of the carbohydrate esterases in the CAZy classification system and are presumed to target ester bonds between lignin alcohols and (4-O-methyl-)d-glucuronic acid residues of xylan. Few GEs have been cloned, expressed and characterised to date. Characterisation has been done on a variety of synthetic substrates; however, the number of commercially available substrates is very limited. We identified novel putative GEs from a wide taxonomic range of fungi and expressed the enzymes originating from Acremonium alcalophilum and Wolfiporia cocos as well as the previously described PcGE1 from Phanerochaete chrysosporium. All three fungal GEs were active on the commercially available compounds benzyl glucuronic acid (BnGlcA), allyl glucuronic acid (allylGlcA) and to a lower degree on methyl glucuronic acid (MeGlcA). The enzymes showed pH stability over a wide pH range and tolerated 6-h incubations of up to 50 °C. Kinetic parameters were determined for BnGlcA. This study shows the suitability of the commercially available model compounds BnGlcA, MeGlcA and allylGlcA in GE activity screening and characterisation experiments. We enriched the spectrum of characterised GEs with two new members of a relatively young enzyme family. Due to its biotechnological significance, this family deserves to be more extensively studied. The presented enzymes are promising candidates as auxiliary enzymes to improve saccharification of plant biomass.Electronic supplementary materialThe online version of this article (doi:10.1007/s00253-017-8266-9) contains supplementary material, which is available to authorized users.

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Section: Introductionmentioning

confidence: 99%

Characterisation of three fungal glucuronoyl esterases on glucuronic acid ester model compounds

Hüttner

Klaubauf

Vries

et al. 2017

Appl Microbiol Biotechnol

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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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“…Some results were already obtained. The synthesis of D-glucuronic acid fatty esters, a novel class of biosurfactants, was achieved by direct esterification in a non-aqueous phase using an immobilized lipase from Candida antarctica (Moreau et al 2004). Lipase-catalysed esterification has been performed in hexane in view to generate novel mixtures of fatty acid esters from specially chosen combinations of fatty acids and alcohols that may be help-full in the preparation of ester flavours for use in food industry (Kim et al 1998).…”

Section: Introductionmentioning

confidence: 99%

Biodegradation of diesel oil and production of fatty acid esters by a newly isolated Pseudomonas citronellolis KHA

Sadouk

Tazerouti

Hacène

2008

World J Microbiol Biotechnol

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The ability of a newly isolated Pseudomonas citronellolis KHA to degrade diesel oil and to synthesize fatty acid esters has been screened in aerobic batch cultures. The microorganism was able to grow with diesel oil at initial concentrations up to 126 g/l, with optimal growth at 25 g/l. Strain KHA has produced compounds showing strong emulsifying properties (E 24 = 75% at the end of the exponential growth phase). The crude extract reduces the surface tension of water from 72 mN m -1 down to 35 mN m -1 with a corresponding minimal concentration value of 60 mg/l. GC and GC-MS analysis of crude product show that the major components are those of hexadecanoic acid propyl ester and octadecanoic acid propyl ester, which have potential for applications in cosmetics, pharmaceutical and foods industries. In addition, strain KHA represents a valuable source of compounds with surface-active properties and potential for the application in clean up of the sites contaminated with hydrocarbons.

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Synthesis of novel d-glucuronic acid fatty esters using Candida antarctica lipase in tert-butanol

Abstract: Glucuronic acid n-alkyl esters, a novel class of promising biosurfactants and their corresponding glucose esters with the same side-chain length, were synthesized by direct esterification in a non-aqueous phase (tert-butanol) using an immobilized lipase.

Cited by 21 publications

References 9 publications

Characterisation of three fungal glucuronoyl esterases on glucuronic acid ester model compounds

Characterisation of three fungal glucuronoyl esterases on glucuronic acid ester model compounds

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

Biodegradation of diesel oil and production of fatty acid esters by a newly isolated Pseudomonas citronellolis KHA

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