Synthèse enzymatique de surfactants sucrés en milieux organiques et dans le CO2 supercritique

Poster (2010, May 18)

Lipase-assisted synthesis of potential bio-based surfactants starting from lignocellulosic carbohydrates

Poster (2010, April)

Surfactants constitute an important class of compounds with a lot of applications, especially in the food and beverage industries (emulsion forming and stabilization, antiadhesive and antimicrobial ... [more ▼]

Surfactants constitute an important class of compounds with a lot of applications, especially in the food and beverage industries (emulsion forming and stabilization, antiadhesive and antimicrobial activities)1. With the prospect of synthesising new active compounds, white biotechnology offers efficient tools. Indeed, the use of enzymes as biocatalysts provides an interesting synthetic route in comparison to the chemical way that often requires high reaction temperatures and suffers from a lack of specificity, resulting in complex mixtures. Among all the biocatalysts available, lipases represent a class of industrial interest 2,3. In parallel, the starting material is also an important parameter : due to the depletion of petroleum reserves, its ever increasing price and various environmental aspects, the use of renewable or biomass resources is inevitable. Within the frame of a biorefinery project, we focused on the lipase-assisted modification of uronic acids. These carbohydrates can be obtained from lignocellulosic material, and, in the presence of fatty alcohols, the Candida antarctica lipase B catalyses the synthesis of amphiphilic compounds. Owing to the initial conditions used and the addition of co-solvents, we optimized the synthesis of these bio-based potential surfactants, and obtained a panel of various structures depending to the acyl acceptor used. The poster will present the details of these syntheses. [less ▲]

Synthèse enzymatique de surfactants sucrés dans le CO2 supercritique

Poster (2009, October 15)

Les esters de carbohydrates sont des surfactants non ioniques ayant un vaste éventail d’applications commerciales en particulier dans l’industrie cosmétique, alimentaire et pharmaceutique. Ils sont ... [more ▼]

Les esters de carbohydrates sont des surfactants non ioniques ayant un vaste éventail d’applications commerciales en particulier dans l’industrie cosmétique, alimentaire et pharmaceutique. Ils sont produits à partir de matières premières renouvelables et peu coûteuses, et sont biodégradables et non toxiques. De manière générale, la synthèse d’esters de sucre nécessite de nombreuses étapes de protection/déprotection des groupements hydroxyles, le nombre et la position exacte des substituants greffés sur un squelette osidique étant des paramètres difficiles à contrôler lors des réactions chimiques. En revanche, la spécificité de certaines enzymes, et en particulier des lipases, peut être mise à profit pour modifier les sucres en milieux organiques. L’utilisation des lipases permet ainsi un meilleure sélectivité et énantiosélectivité des réactions d’estérification et de transestérification. D’autre part, la voie enzymatique permet d’effectuer ces réactions dans des conditions expérimentales beaucoup plus douces de température, de pH et de pression, par rapport aux synthèses réalisées à l’aide de catalyseurs chimiques. Le dioxyde de carbone supercritique (Sc-CO2), quant à lui, constitue une alternative intéressante aux solvants organiques couramment utilisés dans ce domaine car il est non toxique, chimiquement inerte, non inflammable…. Par exemple, son utilisation réduit la contamination des produits finaux avec des solvants résiduels. Ces avantages lui confèrent un large potentiel d’applications notamment dans l’industrie alimentaire, cosmétique, pharmaceutique mais également des matériaux. Notre travail consiste donc à développer la synthèse enzymatique de surfactants sucrés en milieu Sc-CO2 et d’étudier l’influence de divers paramètres sur la réaction biocatalysée. L’activité enzymatique et les rendements observés lors de nos expériences préliminaires dans le Sc-CO2 seront présentés ici et comparés avec ceux obtenus dans des solvants organiques traditionnels. [less ▲]

Enzymatic modifications of sugar in supercritical carbon dioxide

Poster (2009, July 07)

Carbohydrates esters are non-ionic surfactants that have a wide range of commercial applications in cosmetic, food and pharmaceutical industry. They are produced from renewable and inexpensive raw ... [more ▼]

Carbohydrates esters are non-ionic surfactants that have a wide range of commercial applications in cosmetic, food and pharmaceutical industry. They are produced from renewable and inexpensive raw materials, are bio-degradable and non-toxic. Chemical synthesis of sugar esters is generally performed at a high temperature in the presence of an alkaline catalyst lead-ing to a mixture of products. In this respect, the corresponding enzyme-catalyzed processes in non-conventional media are more selective. For this purpose, lipases are the most useful enzymes. Moreover, supercritical carbon dioxide (SC-CO2) constitutes an interesting alternative to the organic solvents used in the domain as it is considered to be environmentally frien-dlier and safer. For example, its use reduces the contamination of the final products with residual solvents. This property is particularly valued in food, cosmetic and pharmaceutical industry. Our work consists to carry out lipase catalyzed sugar modifications in SC-CO2 and to compare the results with those obtained in organic solvents. The effect of these two different media on the enzyme stability and the yield will be described here. Moreover, the impact of various factors such as pressure, temperature, enzyme form (free or immobilized), use of co-solvent, on the course of the sugar esterification will be discussed. [less ▲]

Surface Properties Of New Virginiamycin M-1 Derivatives

in Colloids and Surfaces B : Biointerfaces (2009), 69(2),

Effect of Cholesterol and Fatty Acids on the Molecular Interactions of Fengycin with Stratum Corneum Mimicking Lipid Monolayers.

in Langmuir : the ACS journal of surfaces and colloids (2009), 25

Effect of extraction conditions on the yield and purity of apple pomace pectin precipitated but not washed by alcohol

in Journal of Food Science (2007), 72(1), 1-9

A study of the influence of extraction condition (pH: 1.5 to 2; temperature: 80 to 90 degrees C; extraction time: 1 to 3 h), on the yield and purity of apple pomace pectin without elimination of ... [more ▼]

A study of the influence of extraction condition (pH: 1.5 to 2; temperature: 80 to 90 degrees C; extraction time: 1 to 3 h), on the yield and purity of apple pomace pectin without elimination of impurities by alcohol washing was carried out. The alcohol precipitate yields varied from 2.9% to 8.9% depending on the pH. At pH 1.5, these yields were higher than those obtained at pH 2 contrary to the galacturonic acid purity (%w/w). Compounds other than pectins were solubilized from the cell walls of apple pomace at pH 1.5, and they were precipitated with alcohol. The apple pectins obtained from the different extraction procedures were highly methylated (54.5% to 79.5%), especially when the conditions (temperature, pH) were drastic. Similar conclusions can be drawn for the neutral sugar content that decreased at pH 1.5 (arabinose, xylose, and galactose) or at the highest temperatures and extraction times (arabinose and galactose). The phenomenon of demethylation and pectin degradation of neutral sugars chains can be observed at acid pH, and long extraction times. The presence of high quantities of mannose or fructose, glucose, and xylose in the alcohol precipitate showed that pectin precipitation with ethanol was not specific. [less ▲]

Hemolytic activity of new linear surfactin analogs in relation to their physico-chemical properties

in Biochimica et Biophysica Acta - General Subjects (2005), 1726

New linear analogs of surfactin have been synthesized. Their physico-chemical parameters were determined. The results indicate that these linear products show surface activities although they are lowered ... [more ▼]

New linear analogs of surfactin have been synthesized. Their physico-chemical parameters were determined. The results indicate that these linear products show surface activities although they are lowered compared to those of cyclic compounds. The hemolytic activities have also been assayed. In contrast with cyclic surfactins, no significant hemolysis occurs for the linear products in the range of concentrations tested. Moreover, a protective effect against Triton X-100 induced hemolysis has been highlighted for linear surfactins. The concentration at which this protective effect happens is correlated directly to the CMC, and inversely to the acyl chain length of the product. In a hypotonic medium, analogs having a long acyl chain tend to increase the hemolysis, meanwhile the product with the shortest chain tends to decrease it. [less ▲]

A Chemoselective Ligation For The Synthesis Of Amino Acid Derivatives Of Virginiamycin M-1

in Tetrahedron Letters (2005), 46(43),

Imaging Mixed Lipid Monolayers By Dynamic Atomic Force Microscopy

in Biochimica et Biophysica Acta-Biomembranes (2001), 1513(1),

Phase imaging with tapping mode atomic force microscopy (AFM) and force modulation microscopy were used to probe the mechanical properties of phase-separated lipid monolayers made of a mixture (0.25:0.75 ... [more ▼]

Phase imaging with tapping mode atomic force microscopy (AFM) and force modulation microscopy were used to probe the mechanical properties of phase-separated lipid monolayers made of a mixture (0.25:0.75) of the surface-active lipopeptide surfactin and of dipalmitoylphosphatidylcholine (DPPC). The π–A isotherms and the result of a molecular modeling study revealed a loose, 2-D liquid-like organization for the surfactin molecules and a closely packed, 2-D solid-like organization for DPPC molecules. This difference in molecular organization was responsible for a significant contrast in height, tapping mode phase and force modulation amplitude images. Phase imaging at light tapping, i.e., with a ratio of the set-point tapping amplitude with respect to the free amplitude Asp/A0≈0.9, showed larger phase shifts on the solid-like DPPC domains attributed to larger Young’s modulus. However, contrast inversion was observed for Asp/A0<0.7, suggesting that at moderate and hard tapping the image contrast was dominated by the probe–sample contact area. Surprisingly, force modulation amplitude images showed larger stiffness for the liquid-like surfactin domains, suggesting that the contrast was dominated by contact area effects rather than by Young’s modulus. These data emphasize the complex nature of the contrast mechanisms of dynamic AFM images recorded on mixed lipid monolayers. [less ▲]