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Classical Procedures (classical + procedure)

Distribution by Scientific Domains

Chemistry	50%

Selected Abstracts

Elimination and exchange of trifluoroacetate counter-ion from cationic peptides: a critical evaluation of different approaches

JOURNAL OF PEPTIDE SCIENCE, Issue 3 2008
Stéphane Roux
Abstract Most synthesized peptides are nowadays produced using solid-phase procedures. Due to cleavage and purification conditions, they are mainly obtained in the presence of trifluoroacetic acid (TFA) and, for cationic peptides, as trifluoroacetate (TF-acetate) salts. However, TF-acetate interferes with physicochemical characterizations using infrared spectroscopy and might significantly affect the in vivo studies. Thus, TF-acetate exchange by another counter-ion is often required. Up to now, the classical procedure has consisted of freeze-drying the peptide several times in the presence of an excess of a stronger acid than TFA (pKa ,0): generally HCl (pKa = , 7). This approach means that working at pH < 1 can induce peptide degradation. We therefore tested three different approaches to exchange the tightly bound TF-acetate counter-ion from the dicationic octapeptide lanreotide: (i) reverse-phase HPLC, (ii) ion-exchange resin, and (iii) deprotonation/reprotonation cycle of the amino groups. The first two approaches allow the partial to almost complete exchange of the TF-acetate counter-ion by another ion from an acid weaker than TFA, such as acetic acid (pKa = 4.5), and the third requires a basic solution that permits the complete removal of TF-acetate counter-ion. The efficiency of these three procedures was tested and compared by using different analytical techniques such as 19F-NMR, 1H-NMR and attenuated total reflectance Fourier transformed infrared spectroscopy (ATR FT-IR). We also show that ATR-IR can be used to monitor the TFA removal. The counter-ion exchange procedures described in this study are easy to carry out, fast, harmless and reproducible. Moreover, two of them offer the very interesting possibility of exchanging the initial TF-acetate by any other counter-ion. Copyright © 2007 European Peptide Society and John Wiley & Sons, Ltd. [source]

Multivariate homogeneity testing in a northern case study in the province of Quebec, Canada

HYDROLOGICAL PROCESSES, Issue 12 2009
Fateh Chebana
Abstract In regional frequency analysis, the examination of the regional homogeneity represents an important step of the procedure. Flood events possess multivariate characteristics which can not be handled by classical univariate regional procedures. For instance, classical procedures do not allow to assess regional homogeneity while taking into consideration flood peak, volume and duration. Chebana and Ouarda proposed multivariate discordancy and homogeneity tests. They carried out a simulation study to evaluate the performance of these tests. In the present paper, practical aspects are investigated jointly on flood peak and flood volume of a data set from the Côte-Nord region in the province of Quebec, Canada. It is shown that, after removing the discordant sites, the remaining ones constitute a homogeneous region for the volumes and heterogeneous region for the peaks. However, if both variables are jointly considered, the obtained region is possibly homogeneous. Furthermore, the results demonstrate the usefulness of the bivariate test to take into account the dependence structure between the variables representing the event, and to take advantage of more information from the hydrograph. Copyright © 2009 John Wiley & Sons, Ltd. [source]

Eco-friendly methodologies for the synthesis of some aromatic esters, well-known cosmetic ingredients

INTERNATIONAL JOURNAL OF COSMETIC SCIENCE, Issue 1 2005
C. Villa
Synopsis Solid,liquid solvent-free phase transfer catalysis (PTC) and acidic catalysis in dry media were applied, with noticeable improvement and simplification over classical procedures in a Green Chemistry context, to the synthesis of some aromatic esters useful as cosmetic ingredients: 3-methylbutyl 4-methoxycinnamate, 2-ethylhexyl 4-methoxycinnamate, 2-ethylhexyl 4-(dimethylamino)benzoate and 2-ethylhexyl salicylate, well-known ultraviolet B sunscreen filters; 4-isopropylbenzyl salicylate, UV absorber and cutaneous antilipoperoxidant; propyl 4-hydroxybenzoate and butyl 4-hydroxybenzoate (parabens), antimicrobial agents. The reactions were performed under microwave (MW) activation and conventional heating. The best results for the synthesis of cinnamic, salicylic and 4-(dimethylamino)benzoic esters were achieved by in situ preformed carboxylates alkylation with alkyl bromides using PTC. The 4-hydroxybenzoates were obtained in good yields by classical esterification of the acid with alcohols using a simple heterogeneous mixture of reagents with catalytic amounts of p -toluenesulfonic acid (PTSA). The comparisons of yields and thermal profiles under either MW or conventional heating were studied and reported. Résumé La catalyse par transfert de phase (CTP) solide-liquide sans solvant et l'estérification acido-catalysée en ,,milieu sec'' ont été appliquées, dans le cadre de la ,,chimie verte'', avec des nettes améliorations et simplifications par rapport aux méthodes classiques, à la synthèse de certains esters aromatiques, ingrédients cosmétiques: 3-methylbutyl 4-méthoxycinnamate, 2-éthylhéxyl 4-méthoxycinnamate, 2-éthylhéxyl 4-(diméthylamino) benzoate et 2-éthylhéxyl salicylate, filtres solaires UVB bien connus; 4-isopropylbenzyl salicylate, filtre UV et antilipopéroxydant cutané; propyl 4-hydroxybenzoate et butyl 4-hydroxybenzoate (parabens), agents antimicrobien. Les réactions ont été procédées sous irradiation micro-onde et par chauffage classique. Pour la synthèse des esters dérivés de l'acide cinnamique, salicylique et 4-(diméthylamino)benzoïque les meilleurs résultats ont été obtenus grâce à la CTP par alkylation des carboxylates (préformés in situ) avec des bromures d'alkyle. Les esters de l'acide 4-hydroxybenzoique ont été obtenus avec de bons rendements par simple mélange hétérogène des réactifs et d'acide p-toluènesulfonique (PTSA) comme catalyseur. Les rendements et les profils de montée en température sous micro-ondes et par chauffage classique ont été comparés. [source]

Kinetic and Thermodynamic Solubility Values of Some Bioactive Compounds

CHEMISTRY & BIODIVERSITY, Issue 11 2009
Elham Shoghi
Abstract Thermodynamic solubility is a decisive physicochemical property in drug development. The Chasing Equilibrium method offers an alternative to the classical procedures to measure the solubility of compounds with acid,base properties. The method is fast and yields accurate results. In this work, the solubility of several compounds including acids and bases was determined through the Chasing Equilibrium approach. A study of experimental conditions in terms of sample weight was performed to measure solubilities. The study shows that only a limited range of weights, depending on the nature and solubility of the compounds, is adequate to obtain reliable results. [source]