Synthesis, characterization and functional properties of galactosylated derivatives of chitosan through amide formation

Ana I. Ruiz Matute, Alejandra Cardelle-Cobas, Ana B. García-Bermejo, Antonia Montilla, Agustin Olano, Nieves Corzo*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

47 Citations (Scopus)


Low molecular weight chitosan (LMWC) and chitooligosaccharide (COS) derivatives were obtained by the introduction of lactobionic acid (LA) through amide formation, obtaining different complexes COS-LA and LMWC-LA (1-5), with a degree of substitution (DS) between 3 and 16%. The synthesis of these derivatives was monitored by Scanning Electron Microscopy (SEM), Fourier Transform Infrared Spectroscopy (FT-IR), High-Performance Liquid Chromatography-Size Exclusion Chromatography (HPLC-SEC) and proton Nuclear Magnetic Resonance (1H NMR) analyses. Different functional properties, solubility, water binding capacity (WBC) and fat binding capacity (FBC), as well as the antioxidant activity (DPPH radical scavenging activity) of these derivatives were evaluated. Solubility, WBC and FBC increased in all of the chitosan derivatives respect to those of the native LMWC or COS. The most substituted derivative (LMWC-LA1, DS 15%) presented the highest value of solubility (14.4mg/mL) while the highest levels of WBC and FBC were obtained for the derivative with a DS of 3% (LMWC-LA5; 4730% and 7100%, respectively). COS and COS-LA presented the best DPPH scavenging abilities, as shown by their low values of EC50 (1.29 and 3.45mg/mL, respectively). An inverse relationship between the DS of chitosan derivatives and antioxidant activity was observed. LMWC-LA5 (3% DS) was the derivative with the highest DPPH activity, being higher than LMWC in all the concentrations assayed (10.2-14.3% and 6.9-13.7%, respectively). Due to their enhanced functional properties, these chitosan derivatives could be considered as very promising for their future use as additives in the food industry (i.e. to bind fat and cholesterol or avoid hardening of foods).
Original languageEnglish
Pages (from-to)245-255
Number of pages11
JournalFood Hydrocolloids
Issue number2
Publication statusPublished - Dec 2013


  • Chitooligosaccharides
  • Chitosan
  • Functional properties
  • Glycosylation
  • Lactobionic acid


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