D-Xylose and L-arabinose laurate esters: Enzymatic synthesis, characterization and physico-chemical properties

Efficient enzymatic synthesis of D-xylose and L-arabinose lauryl mono- and diesters has been achieved by transesterification reactions catalysed by immobilized Candida antarctica lipase B as biocatalyst, in organic medium in the presence of D-xylose or L-arabinose and vinyllaurate at 50°C. In case of L-arabinose, one monoester and one diester were obtained in a 57% overall yield. A more complex mixture was produced for Dxylose as two monoesters and two diesters were synthesized in a 74.9% global yield. The structures of all these pentose laurate esters was solved. Results demonstrated that the esterification first occurred regioselectively onto the primary hydroxyl groups. Pentose laurate esters exhibited interesting features such as low critical aggregation concentrations values all inferior to 25μM. Our study demonstrates that the enzymatic production of L-arabinose and D-xylose-based esters represents an interesting approach for the production of green surfactants from lignocellulosic biomass-derived pentoses

Synthesis of D- and L-erythro 1,5-dithiopent-1-enopyranoside sulfonium salts and their evaluation as glycosidase inhibitors

A series of sulfonium salts derived from 1,5-dithiopent-1-enopyranosides was prepared in a three-step sequence from protected D- and L-erythrofuranoses. The key step is the nucleophilic displacement of a leaving group by a sulfur atom of carbohydrate-derived ketene dithioacetals. Such compounds were assayed for their properties as glycosidase inhibitors. (C) 2009 Elsevier Ltd. All rights reserved

Fluorophosphonylated Nucleoside Derivatives as New Series of Thymidine Phosphorylase Multisubstrate Inhibitors

International audienceThe synthesis of new class of potential TPase inhibitors containing a difluoromethylphosphonate function as phosphate mimic is reported. This new series was prepared from a readily available fluorinated building block in few steps. Two series were evaluated as potential inhibitors: a linear series and a conformational constrained series. The activity of these multisubstrate inhibitors depends on the size of the spacer introduced between the pyrimidine ring and the phos- phonate function. Best results were observed from triazolyl derivatives, easily obtained from propargylthymine and corresponding azides

Perfluoroketene dithioacetals and perfluorodithiocarboxylic acid derivatives: Versatile tools for organofluorine synthesis

International audienc

Fluorophosphonylated Nucleoside Derivatives as New Series of Thymidine Phosphorylase Multisubstrate Inhibitors

The synthesis of new class of potential TPase inhibitors containing a difluoromethylphosphonate function as phosphate mimic is reported. This new series was prepared from a readily available fluorinated building block in few steps. Two series were evaluated as potential inhibitors: a linear series and a conformational constrained series. The activity of these multisubstrate inhibitors depends on the size of the spacer introduced between the pyrimidine ring and the phosphonate function. Best results were observed from triazolyl derivatives, easily obtained from propargylthymine and corresponding azides

Chimie du végétal et produits innovants à forte valeur ajoutée

International audienceCes vingt-cinq dernières années ont vu émerger la possibilité d’une société reposant sur un apport carboné biosourcé en remplacement du carbone fossile, transition souvent appelée à tort « société décarbonée ». Le territoire champardennais, terre agricole, s’est engagé dès les années 1990 dans une démarche de bioraffinerie durable en associant recherche académique et acteurs économiques et politiques.C’est dans ce contexte que s’est développée une recherche en chimie du végétal tournée vers les secteurs à moyenne ou haute valeur ajoutée en visant des produits de spécialité ou des actifs originaux et performants dans des domaines aussi variés que les matériaux, la chimie fine, l’environnement, l’agrochimie, la santé ou la cosmétique