Novel highly-soluble peptide–chitosan polymers: Chemical synthesis and spectral characterization

• Published in: Carbohydrate polymers Vol. 64; no. 2; pp. 299 - 305
• Main Authors: Batista, M.K.S., Pinto, L.F., Gomes, C.A.R., Gomes, P.
• Format: Journal Article
• Language: English
• Published: Oxford Elsevier Ltd 11.05.2006; Elsevier Science
• Subjects: Applied sciences; aspartic acid; chemical analysis; Chitosan; Exact sciences and technology; N-(-y-propanoyl-aspartic acid)-chitosan; N-(-y-propanoyl-valine)-chitosan; N-(γ-propanoyl-aspartic acid)-chitosan; N-(γ-propanoyl-valin)-chitosan; Natural polymers; Peptide; peptides; physical properties; Physicochemistry of polymers; Polymer; polymers; spectral analysis; Starch and polysaccharides; synthesis; valine; water solubility; N-(γ-propanoyl-valin)-chitosan; Polymer; Chitosan; N-(γ-propanoyl-aspartic acid)-chitosan; Peptide; Molecular structure; Mild operating conditions; Experimental study; Lateral group; Chemical coupling; Polyelectrolyte; Chemical modification; Chitosan derivatives; Preparation; Oside polymer; Soluble compound; Polyacid; Growth from solution; N-(y-propanoyl-valin)-chitosan
• ISSN: 0144-8617; 1879-1344
• DOI: 10.1016/j.carbpol.2005.11.040

Novel water-soluble polymers, N-(γ-propanoyl-valin)-chitosan and N-(γ-propanoyl-aspartic acid)-chitosan, were synthesized by reaction of low molecular weight chitosan with N α-(3-bromopropanoyl)-valine and N α-(3-bromopropanoyl)-aspartic acid, respectively, under mild conditions. Prior to reaction with chitosan, the peptide substituents have been prepared by standard peptide chemistry methods from 3-bromopropanoic acid and the relevant α-amino acid tert-butyl esters. The chemical structure and physical properties of the novel chitosan derivatives were characterized by 1H NMR and IR spectroscopy. The polymers are highly soluble in a wide pH range, which opens new perspectives for the applications of chitosan-based materials.