Investigation of the effects of various parameters on the synthesis of oligopeptides in aqueous solution |
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Authors: | Sagrario Pascual David M. Haddleton Ezat Khoshdel |
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Affiliation: | a LCOM-Chimie des Polymères, Université du Maine, Avenue Olivier Messiaen, 72085 Le Mans Cedex 9, France b Department of Chemistry, University of Warwick, Coventry CV4 7AL, UK c Unilever Research, Port Sunlight, Bebington CH63 3JW, UK |
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Abstract: | Oligomerization efficiency of amino acids in aqueous solution has been compared under different conditions (temperature, activating agent, etc.) using 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC) and 1,1′-carbonyldiimidazole (CDI) as coupling agents. Glycine (H2N-CH2-COOH) and α-alanine (H2N-CH(CH3)-COOH) were chosen as α-amino acids and β-alanine (H2N-CH2-CH2-COOH) as the β-amino acid. The coupling reaction between EDC and glycine was shown to occur but does not go to completion either at ambient temperature or at 70 °C. The presence of a carboxylic activating agent such as N-hydroxysuccinimide improves the EDC-mediated coupling reaction, and the amino acid structure (α- or β-) was shown to have an influence on the oligomerization efficiency, with β-alanine polymerisation being more efficient. These findings are explained by reference to the reaction mechanism. |
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Keywords: | 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide N-hydroxysuccinimide Oligopeptides Aqueous solution |
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