Abstract
UV irradiation hydrogen peroxide (\(\hbox {H}_{2} \hbox {O}_{2}\)) system is used as an effective, easy and low-cost combined depolymerization technique to produce oligosaccharides from chitosan. UV–Vis spectroscopic studies explained that with increasing treatment time, the absorption of the depolymerized chitosan solution has increased, indicating the increase in the carbonyl and amino groups in their structure. Fourier transform infrared spectroscopy and nuclear magnetic resonance (1H NMR) analysis showed that the 1,4-\(\beta \)-d-glucoside linkages of chitosan are degraded without important changes in chemical structure of decomposed samples. X-ray diffraction patterns verified the polymerization of chitosan to produce oligomers, changing in structure from crystalline to amorphous. Viscosity-average molecular weight measurements of fragmented chitosan samples and Mark–Houwink equation are used to demonstrate the efficiency of this depolymerization method. Finally, the obtained results ascertained that this combined method could produce water soluble chitosan with significant efficiency and no essential change in its chemical structure.
References
Usman A, Zia KM, Zuber M, Tabasum S, Rehman S, Zia F (2016) Chitin and chitosan based polyurethanes: a review of recent advances and prospective biomedical applications. Int J Biol Macromol 86:630–645
Baldwin AD, Kiick KL (2010) Polysaccharide-modified synthetic polymeric biomaterials. Pept Sci 94(1):128–140
Suh S, Kim S, Lee Y, Kim J (1994) Synthesis and characteristics of trimethylsilyl chitin. Polym Korea 18:906–906
Younes I, Hajji S, Frachet V, Rinaudo M, Jellouli K, Nasri M (2014) Chitin extraction from shrimp shell using enzymatic treatment. Antitumor, antioxidant and antimicrobial activities of chitosan. Int J Biol Macromol 69:489–498
Barikani M, Honarkar H, Barikani M (2010) Synthesis and characterization of chitosan-based polyurethane elastomer dispersions. Monatshefte für Chemie-Chemical Monthly 141(6):653–659
Heidari F, Razavi M, Bahrololoom ME, Tahriri M, Rasoulianboroujeni M, Koturi H, Tayebi L (2016) Preparation of natural chitosan from shrimp shell with different deacetylation degree. Mater Res Innov 1–5
Periayah MH, Halim AS, Saad AZM (2016) Chitosan: a promising marine polysaccharide for biomedical research. Pharmacogn Rev 10(19):39
Subhapradha N, Ramasamy P, Shanmugam V, Madeswaran P, Srinivasan A, Shanmugam A (2013) Physicochemical characterisation of \(\beta \)-chitosan from Sepioteuthis lessoniana gladius. Food Chem 141(2):907–913
Honarkar H, Barikani M (2009) Applications of biopolymers I: chitosan. Monatshefte für Chemie-Chemical Monthly 140(12):1403
Ayati Najafabadi S, Keshvari H, Ganji Y, Tahriri M, Ashuri M (2012) Chitosan/heparin surface modified polyacrylic acid grafted polyurethane film by two step plasma treatment. Surf Eng 28(9):710–714
Barikani M, Honarkar H, Barikani M (2009) Synthesis and characterization of polyurethane elastomers based on chitosan and poly (\(\varepsilon \)-caprolactone). J Appl Polym Sci 112(5):3157–3165
Davoudi Z, Rabiee M, Houshmand B, Eslahi N, Khoshroo K, Rasoulianboroujeni M, Tahriri M, Tayebi L (2018) Development of chitosan/gelatin/keratin composite containing hydrocortisone sodium succinate as a buccal mucoadhesive patch to treat desquamative gingivitis. Drug Dev Ind Pharm 44(1):40–55
Najafabadi SAA, Keshvari H, Sarkhosh H, Ashuri M, Tahriri M (2014) Surface modification of castor oil-based polyurethane by polyacrylic acid graft using a two-step plasma treatment for biomedical applications. Adv Polym Technol 33(3):21411–21419
Croisier F, Jérôme C (2013) Chitosan-based biomaterials for tissue engineering. Eur Polymer J 49(4):780–792
Raz M, Moztarzadeh F, Shokrgozar M, Ashuri M, Tahriri M (2013) Preparation, characterization and evaluation of mechanical and biological characteristics of hybrid apatite/gelatin-chitosan nanocomposite bone scaffold via biomimetic method. J Adv Mater Eng (Esteghlal) 32(2):25–42
Emami SH, Abad AMA, Bonakdar S, Tahriri MR, Samadikuchaksaraei A, Bahar MA (2010) Preparation and evaluation of chitosan-gelatin composite scaffolds modified with chondroitin-6-sulphate. Int J Mater Res 101(10):1281–1285
Raz M, Moztarzadeh F, Shokrgozar MA, Azami M, Tahriri M (2014) Development of biomimetic gelatin-chitosan/hydroxyapatite nanocomposite via double diffusion method for biomedical applications. Int J Mater Res 105(5):493–501
Choi C, Ahn J-H, Jeong G-W, Lee H-S, Choi S-J, Kim W-S, Nah J-W (2016) Preparation of nicotinic acid-loaded microspheres using water-soluble. Chitosan and investigation of their physicochemical characteristics. Polym Korea 40(4):643–650
Anusha J, Raj CJ, Cho B-B, Fleming AT, Yu K-H, Kim BC (2015) Amperometric glucose biosensor based on glucose oxidase immobilized over chitosan nanoparticles from gladius of Uroteuthis duvauceli. Sens Actuators B Chem 215:536–543
Xia Z, Wu S, Chen J (2013) Preparation of water soluble chitosan by hydrolysis using hydrogen peroxide. Int J Biol Macromol 59:242–245
Rege PR, Block LH (1999) Chitosan processing: influence of process parameters during acidic and alkaline hydrolysis and effect of the processing sequence on the resultant chitosan’s properties. Carbohydr Res 321(3):235–245
Huang QZ, Meng ZH, Feng YQ, Shi HZ (2010) Study on the heterogeneous degradation of chitosan with \({\rm H}_2{\rm O}_2\) catalyzed by a new supermolecular assembly crystal:[C\(_6\)H\(_8\)N\(_2\)]6H\(_3\)[PW\(_{12}\)O\(_{40}\)] \(\cdot \) 2H\(_2\)O. Carbohydr Res 345(1):115–119
Qin C, Du Y, Xiao L (2002) Effect of hydrogen peroxide treatment on the molecular weight and structure of chitosan. Polym Degrad Stab 76(2):211–218
Xie Y, Hu J, Wei Y, Hong X (2009) Preparation of chitooligosaccharides by the enzymatic hydrolysis of chitosan. Polym Degrad Stab 94(10):1895–1899
Lee J-J, Lee W-H, Shin Y-I, Paek S-H (2012) Effects of UV irradiation and thermal treatment of photo-degradable polyimide layer on LC alignment. Polym Korea 36(2):145–148
Ma F, Wang Z, Zhao H, Tian S (2012) Plasma depolymerization of chitosan in the presence of hydrogen peroxide. Int J Mol Sci 13(6):7788–7797
Choi S-K, Choi Y-S (2011) Depolymerization of alginates by hydrogen peroxide/ultrasonic irradiation. Polym Korea 35(5):444–450
Kang B, Dai Y-D, Zhang H-Q, Chen D (2007) Synergetic degradation of chitosan with gamma radiation and hydrogen peroxide. Polym Degrad Stab 92(3):359–362
Huei CR, Hwa H-D (1996) Effect of molecular weight of chitosan with the same degree of deacetylation on the thermal, mechanical, and permeability properties of the prepared membrane. Carbohydr Polym 29(4):353–358
Knaul JZ, Kasaai MR, Bui VT, Creber KA (1998) Characterization of deacetylated chitosan and chitosan molecular weight review. Can J Chem 76(11):1699–1706
Yue W (2014) Prevention of browning of depolymerized chitosan obtained by gamma irradiation. Carbohydr Polym 101:857–863
Andrady AL, Torikai A, Kobatake T (1996) Spectral sensitivity of chitosan photodegradation. J Appl Polym Sci 62(9):1465–1471
Sionkowska A, Płanecka A, Lewandowska K, Kaczmarek B, Szarszewska P (2013) Influence of UV-irradiation on molecular weight of chitosan. Prog Chem Appl Chitin Deriv 18(18):21–28
Li SD, Zhang CH, Dong JJ, Ou CY, Quan WY, Yang L, She XD (2010) Effect of cupric ion on thermal degradation of quaternized chitosan. Carbohydr Polym 81(2):182–187
de Britto D, de Assis OB (2007) Synthesis and mechanical properties of quaternary salts of chitosan-based films for food application. Int J Biol Macromol 41(2):198–203
Huang QZ, Wang SM, Huang JF, Zhuo LH, Guo YC (2007) Study on the heterogeneous degradation of chitosan with hydrogen peroxide under the catalysis of phosphotungstic acid. Carbohydr Polym 68(4):761–765
Li J, Cai J, Zhong L, Du Y (2012) Immobilization of a protease on modified chitosan beads for the depolymerization of chitosan. Carbohydr Polym 87(4):2697–2705
Belamie E, Domard A, Giraud-Guille MM (1997) Study of the solid-state hydrolysis of chitosan in presence of HCl. J Polym Sci A Polym Chem 35(15):3181–3191
Yue W, Yao P, Wei Y (2009) Influence of ultraviolet-irradiated oxygen on depolymerization of chitosan. Polym Degrad Stab 94(5):851–858
Tian F, Liu Y, Hu K, Zhao B (2004) Study of the depolymerization behavior of chitosan by hydrogen peroxide. Carbohydr Polym 57(1):31–37
Dhawade PP, Jagtap RN (2012) Characterization of the glass transition temperature of chitosan and its oligomers by temperature modulated differential scanning calorimetry. Adv Appl Sci Res 3(3):1372
Le Dung P, Milas M, Rinaudo M, Desbrières J (1994) Water soluble derivatives obtained by controlled chemical modifications of chitosan. Carbohydr Polym 24(3):209–214
Duan J, Kasper DL (2010) Oxidative depolymerization of polysaccharides by reactive oxygen/nitrogen species. Glycobiology 21(4):401–409
Tanioka S, Matsui Y, Irie T, Tanigawa T, Tanaka Y, Shibata H, Sawa Y, Kono Y (1996) Oxidative depolymerization of chitosan by hydroxyl radical. Biosci Biotechnol Biochem 60(12):2001–2004
Rees MD, Kennett EC, Whitelock JM, Davies MJ (2008) Oxidative damage to extracellular matrix and its role in human pathologies. Free Radical Biol Med 44(12):1973–2001
Tian F, Liu Y, Hu K, Zhao B (2003) The depolymerization mechanism of chitosan by hydrogen peroxide. J Mater Sci 38(23):4709–4712
Hsu S-C, Don T-M, Chiu W-Y (2002) Free radical degradation of chitosan with potassium persulfate. Polym Degrad Stab 75(1):73–83
Acknowledgements
The work was done in Department of Nutrition and Food Sciences at Isfahan University of Medical Sciences, Iran. We would like to especially thank Mr. Yahaii, for helping to prepare materials. This research did not receive any specific grant from funding agencies in the public, commercial or not-for-profit sectors.
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Najafabadi, S.A.A., Honarkar, H., Moghadam, M. et al. UV irradiation-\(\hbox {H}_{2} \hbox {O}_{2}\) system as an effective combined depolymerization technique to produce oligosaccharides from chitosan. Bio-des. Manuf. 1, 62–68 (2018). https://doi.org/10.1007/s42242-018-0005-2
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DOI: https://doi.org/10.1007/s42242-018-0005-2