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Modification of Chitosan/Chitin and Its Oligosaccharides

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Oligosaccharides of Chitin and Chitosan
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Abstract

In view of rapidly growing interest in the amino polysaccharide chitosan/chitin and its oligosaccharides as functional biopolymer, a recent progress of basic and application studies in chitosan/chitin oligosaccharides chemistry is reviewed as well as some basic aspects of this specialty biomass resource. A special emphasis is placed on the controlled modification reactions to prepare chitin derivatives with well-defined structures and thereby to construct sophisticated molecular architecture having various advanced functions. The reactions discussed here include acylation, quaternary ammonium salt, carboxyalkylation, graft copolymerization, quaternary salt formation, Schiff base formation, reductive alkylation, microwave modification. For conducting modification reactions in a facile and controlled manner, some soluble chitosan/chitin oligosaccharides derivatives are convenient. To fully explore the high potential of these specialty biopolymers, basic and application researches are being made extensively.

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References

  • Acet Ö, Baran T, Erdönmez D, Aksoy NH, Alacabey İ, Menteş A, Odabaşi M (2018) O-carboxymethyl chitosan Schiff base complexes as affinity ligands for immobilized metal-ion affinity chromatography of lysozyme. J Chromatogr A 1550:21–27

    Article  CAS  PubMed  Google Scholar 

  • Aly AA, El-Bisi MK (2018) Chapter 11 – grafting of polysaccharides: recent advances. In: Thakur VK (ed) Biopolymer grafting. Elsevier, Cambridge, MA, pp 469–519

    Chapter  Google Scholar 

  • Avadi MR, Jalali A, Sadeghi AMM, Shamimi K, Bayati KH, Nahid E et al (2005) Diethyl methyl chitosan as an intestinal paracellular enhancer: ex vivo and in vivo studies. Int J Pharm 293(1):83–89

    Article  CAS  PubMed  Google Scholar 

  • Aytemir MD, Ozcelik B (2011) Synthesis and biological activities of new Mannich bases of chlorokojic acid derivatives. Med Chem Res 20:443

    Article  CAS  Google Scholar 

  • Badawy MEI, Rabea EI (2014) Synthesis and antifungal property of N-(aryl) and quaternary N-(aryl) chitosan derivatives against Botrytis cinerea. Cellulose 21(4):3121–3137

    Article  CAS  Google Scholar 

  • Badawy MEI, Rabea EI, Rogge TM, Stevens CV, Smagghe G, Steurbaut W, Höfte M (2004) Synthesis and fungicidal activity of new N,O-acyl chitosan derivatives. Biomacromolecules 5(2):589–595

    Article  CAS  PubMed  Google Scholar 

  • Baran T, Açıksöz E, Menteş A (2016) Highly efficient, quick and green synthesis of biarlys with chitosan supported catalyst using microwave irradiation in the absence of solvent. Carbohydr Polym 142:189–198

    Article  CAS  PubMed  Google Scholar 

  • Bardajee GR, Hooshyar Z, Zehtabi F, Pourjavadi A (2012) A superabsorbent hydrogel network based on poly((2-dimethylaminoethyl) methacrylate) and sodium alginate obtained by γ-radiation: synthesis and characterization. Iran Polym J 21(12):829–836

    Article  CAS  Google Scholar 

  • Bhatnagar A, Sillanpää M (2009) Applications of chitin- and chitosan-derivatives for the detoxification of water and wastewater – a short review. Adv Colloid Interf Sci 152(1):26–38

    Article  CAS  Google Scholar 

  • Bodnar ED, Perreault H (2015) Synthesis and evaluation of carboxymethyl chitosan for glycopeptide enrichment. Anal Chim Acta 891:179–189

    Article  CAS  PubMed  Google Scholar 

  • Bratskaya SY, Azarova YA, Matochkina EG, Kodess MI, Yatluk YG, Pestov AV (2012) N-(2-(2-pyridyl)ethyl)chitosan: synthesis, characterization and sorption properties. Carbohydr Polym 87(1):869–875

    Article  CAS  Google Scholar 

  • Fujii S (1980) Preparation of poly (acyl) chitosans. Carbohydr Res 83:389–393

    Article  CAS  Google Scholar 

  • Gedye R, Smith F, Westaway K, Ali H, Baldisera L, Laberge L, Rousell J (1986) The use of microwave ovens for rapid organic synthesis. Tetrahedron Lett 27(3):279–282

    Article  CAS  Google Scholar 

  • Geisberger G, Gyenge EB, Hinger D, Käch A, Maake C, Patzke GR (2013) Chitosan-thioglycolic acid as a versatile antimicrobial agent. Biomacromolecules 14(4):1010–1017

    Article  CAS  PubMed  Google Scholar 

  • He J, Wang J, Zhong H, Ding J, Zhang L (2015) Cyanoethylated carboxymethyl chitosan as water soluble binder with enhanced adhesion capability and electrochemical performances for LiFePO4 cathode. Electrochim Acta 182:900–907

    Article  CAS  Google Scholar 

  • Hirano S, Zhang M (2000) Cellulose–acidic glycosaminoglycan blend fibers releasing a portion of the glycosaminoglycans in water. Carbohydr Polym 43(3):281–284

    Article  CAS  Google Scholar 

  • Hirano S, Ohe Y, Ono H (1976) Selective N-acylation of chitosan. Carbohydr Res 47(2):315–320

    Article  CAS  PubMed  Google Scholar 

  • Hu F-Q, Zhao M-D, Yuan H, You J, Du Y-Z, Zeng S (2006) A novel chitosan oligosaccharide–stearic acid micelles for gene delivery: properties and in vitro transfection studies. Int J Pharm 315(1–2):158–166

    Article  CAS  PubMed  Google Scholar 

  • Huang J, Chen W-w, Hu S, Gong J-Y, Lai H-W, Liu P et al (2013a) Biochemical activities of 6-carboxy β-chitin derived from squid pens. Carbohydr Polym 91(1):191–197

    Article  CAS  PubMed  Google Scholar 

  • Huang J, Jiang H, Qiu M, Geng X, Yang R, Li J, Zhang C (2013b) Antibacterial activity evaluation of quaternary chitin against Escherichia coli and Staphylococcus aureus. Int J Biol Macromol 52:85–91

    Article  CAS  PubMed  Google Scholar 

  • Huang W, Wang Y, Zhang S, Huang L, Hua D, Zhu X (2013c) A facile approach for controlled modification of chitosan under γ-ray irradiation for drug delivery. Macromolecules 46(3):814–818

    Article  CAS  Google Scholar 

  • Jenkins DW, Hudson SM (2001) Heterogeneous chloroacetylation of chitosan powder in the presence of sodium bicarbonate. J Polym Sci A Polym Chem 39(23):4174–4181

    Article  CAS  Google Scholar 

  • Jenkins DW, Hudson SM (2002) Heterogeneous graft copolymerization of chitosan powder with methyl acrylate using trichloroacetyl−manganese carbonyl co-initiation. Macromolecules 35(9):3413–3419

    Article  CAS  Google Scholar 

  • Jia Z, shen D, Xu W (2001) Synthesis and antibacterial activities of quaternary ammonium salt of chitosan. Carbohydr Res 333(1):1–6

    Article  CAS  PubMed  Google Scholar 

  • Kaifu K, Nishi N, Komai T, Tokura S, Somorin O (1981) Studies on chitin. V. formylation, propionylation, and butyrylation of chitin. Polym J 13:241

    Article  CAS  Google Scholar 

  • Karrer P, White SM (1930) Polysaccharide XLIV. Weitere Beiträge zur Kenntnis des Chitins. Helv Chim Acta 13(5):1105–1113

    Article  CAS  Google Scholar 

  • Konwar A, Kalita S, Kotoky J, Chowdhury D (2016) Chitosan–iron oxide coated graphene oxide nanocomposite hydrogel: a robust and soft antimicrobial biofilm. ACS Appl Mater Interfaces 8(32):20625–20634

    Article  CAS  PubMed  Google Scholar 

  • Kurita K (2001) Controlled functionalization of the polysaccharide chitin. Prog Polym Sci 26(9):1921–1971

    Article  CAS  Google Scholar 

  • Kurita K (2006) Chitin and chitosan: functional biopolymers from marine crustaceans. Mar Biotechnol 8(3):203

    Article  CAS  PubMed  Google Scholar 

  • Kurita K, Ichikawa H, Ishizeki S, Fujisaki H, Iwakura Y (1982) Studies on chitin, 8. Modification reaction of chitin in highly swollen state with aromatic cyclic carboxylic acid anhydrides. Die Makromol Chem 183(5):1161–1169

    Article  CAS  Google Scholar 

  • Kurita K, Ishii S, Tomita K, Nishimura S-I, Shimoda K (1994) Reactivity characteristics of squid β-chitin as compared with those of shrimp chitin: high potentials of squid chitin as a starting material for facile chemical modifications. J Polym Sci A Polym Chem 32(6):1027–1032

    Article  CAS  Google Scholar 

  • Kurita K, Mori S, Nishiyama Y, Harata M (2002) N-alkylation of chitin and some characteristics of the novel derivatives. Polym Bull 48(2):159–166

    Article  CAS  Google Scholar 

  • Li C, Tian H, Rong N, Liu K, Liu F, Zhu Y, Jiang Y (2011) Chitosan grafted with macrocyclic polyamines on C-2 and C-6 positions as nonviral gene vectors: preparation, characterization, and in vitro transfection studies. Biomacromolecules 12(2):298–305

    Article  CAS  PubMed  Google Scholar 

  • Lin Y-H, Liang H-F, Chung C-K, Chen M-C, Sung H-W (2005) Physically crosslinked alginate/N,O-carboxymethyl chitosan hydrogels with calcium for oral delivery of protein drugs. Biomaterials 26(14):2105–2113

    Article  CAS  PubMed  Google Scholar 

  • Liu L, Li Y, Li Y, Fang Y-E (2004) Rapid N-phthaloylation of chitosan by microwave irradiation. Carbohydr Polym 57(1):97–100

    Article  CAS  Google Scholar 

  • Liu X, Xia W, Jiang Q, Xu Y, Yu P (2014) Synthesis, characterization, and antimicrobial activity of Kojic acid grafted chitosan oligosaccharide. J Agric Food Chem 62(1):297–303

    Article  CAS  PubMed  Google Scholar 

  • Liu X, Jiang Q, Xia W (2018a) One-step procedure for enhancing the antibacterial and antioxidant properties of a polysaccharide polymer: Kojic acid grafted onto chitosan. Int J Biol Macromol 113:1125–1133

    Article  CAS  PubMed  Google Scholar 

  • Liu X, Xia W, Jiang Q, Yu P, Yue L (2018b) Chitosan oligosaccharide-N-chlorokojic acid mannich base polymer as a potential antibacterial material. Carbohydr Polym 182:225–234

    Article  CAS  PubMed  Google Scholar 

  • LogithKumar R, KeshavNarayan A, Dhivya S, Chawla A, Saravanan S, Selvamurugan N (2016) A review of chitosan and its derivatives in bone tissue engineering. Carbohydr Polym 151:172–188

    Article  CAS  PubMed  Google Scholar 

  • Loubaki E, Sicsic S, Le Goffic F (1989) Modification chimique du chitosane avec la δ-gluconolactone, la β-propiolactone et le glycidol. Eur Polym J 25(4):379–384

    Article  CAS  Google Scholar 

  • Muzzarelli RAA, Tanfani F, Emanuelli M, Mariotti S (1982) N-(carboxymethylidene)chitosans and N-(carboxymethyl)chitosans: novel chelating polyampholytes obtained from chitosan glyoxylate. Carbohydr Res 107(2):199–214

    Article  CAS  Google Scholar 

  • Ning Ma AW (2004) Progress in chemical modification of chitin and chitosan. Prog Chem 16(4):643–653. In Chinese

    Google Scholar 

  • Nishimura S-I, Kai H, Shinada K, Yoshida T, Tokura S, Kurita K et al (1998) Regioselective syntheses of sulfated polysaccharides: specific anti-HIV-1 activity of novel chitin sulfates. Carbohydr Res 306(3):427–433

    Article  CAS  PubMed  Google Scholar 

  • Pillai CKS, Paul W, Sharma CP (2009) Chitin and chitosan polymers: chemistry, solubility and fiber formation. Prog Polym Sci 34(7):641–678

    Article  CAS  Google Scholar 

  • Popescu V, Muresan A, Popescu G, Balan M, Dobromir M (2016) Ethyl chitosan synthesis and quantification of the effects acquired after grafting it on a cotton fabric, using ANOVA statistical analysis. Carbohydr Polym 138:94–105

    Article  CAS  PubMed  Google Scholar 

  • Qizhi Dong ZG (2001) O-alkylation of chitosan under microwave irradiation. Nat Sci J Xiangtan Univ 23(2):57–59. in Chinese

    Google Scholar 

  • Rahmani S, Mohammadi Z, Amini M, Isaei E, Taheritarigh S, Rafiee Tehrani N, Rafiee Tehrani M (2016) Methylated 4-N,N dimethyl aminobenzyl N,O carboxymethyl chitosan as a new chitosan derivative: synthesis, characterization, cytotoxicity and antibacterial activity. Carbohydr Polym 149:131–139

    Article  CAS  PubMed  Google Scholar 

  • Ravi Kumar MNV (2000) A review of chitin and chitosan applications. React Funct Polym 46(1):1–27

    Article  Google Scholar 

  • Rúnarsson ÖV, Holappa J, Malainer C, Steinsson H, Hjálmarsdóttir M, Nevalainen T, Másson M (2010) Antibacterial activity of N-quaternary chitosan derivatives: synthesis, characterization and structure activity relationship (SAR) investigations. Eur Polym J 46(6):1251–1267

    Article  CAS  Google Scholar 

  • Sahariah P, Gaware V, Lieder R, Jónsdóttir S, Hjálmarsdóttir M, Sigurjonsson O, Másson M (2014) The effect of substituent, degree of acetylation and positioning of the cationic charge on the antibacterial activity of quaternary chitosan derivatives. Mar Drugs 12(8):4635

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  • Sahariah P, Benediktssdóttir BE, Hjálmarsdóttir MÁ, Sigurjonsson OE, Sørensen KK, Thygesen MB, Másson M (2015) Impact of chain length on antibacterial activity and hemocompatibility of quaternary N-alkyl and N,N-dialkyl chitosan derivatives. Biomacromolecules 16(5):1449–1460

    Article  CAS  PubMed  Google Scholar 

  • Sangeetha Y, Meenakshi S, SairamSundaram C (2015) Corrosion mitigation of N-(2-hydroxy-3-trimethyl ammonium)propyl chitosan chloride as inhibitor on mild steel. Int J Biol Macromol 72:1244–1249

    Article  CAS  PubMed  Google Scholar 

  • Setia A (2018) Chapter 1 – Applications of graft copolymerization: a revolutionary approach. In: Thakur VK (ed) Biopolymer grafting. Elsevier, Cambridge, MA, pp 1–44

    Google Scholar 

  • Shin-Ichiro N, Yoshiaki M, Longdi R, Manabu S, Akihiko Y, Norio N et al (1993) An efficient method for the syntheses of novel amphiphilic polysaccharides by regio- and thermoselective modifications of chitosan. Chem Lett 22(9):1623–1626

    Article  Google Scholar 

  • Shoda S-i, Uyama H, Kadokawa J-i, Kimura S, Kobayashi S (2016) Enzymes as green catalysts for precision macromolecular synthesis. Chem Rev 116(4):2307–2413

    Article  CAS  PubMed  Google Scholar 

  • Singh DK, Ray AR (2000) Biomedical applications of chitin, chitosan, and their derivatives. J Macromol Sci C 40(1):69–83

    Article  Google Scholar 

  • Singh V, Kumar P, Sanghi R (2012) Use of microwave irradiation in the grafting modification of the polysaccharides – a review. Prog Polym Sci 37(2):340–364

    Article  CAS  Google Scholar 

  • Sini TK, Santhosh S, Mathew PT (2005) Study of the influence of processing parameters on the production of carboxymethylchitin. Polymer 46(9):3128–3131

    Article  CAS  Google Scholar 

  • Thanou M, Nihot MT, Jansen M, Verhoef JC, Junginger HE (2001) Mono-N-carboxymethyl chitosan (MCC), a polyampholytic chitosan derivative, enhances the intestinal absorption of low molecular weight heparin across intestinal epithelia in vitro and in vivo. J Pharm Sci 90(1):38–46

    Article  CAS  PubMed  Google Scholar 

  • Uragami T, Matsuoka Y, Miyata T (2016) Removal of dilute benzene in water through ionic liquid/poly(vinyl chloride) membranes by pervaporation. J Membr Sci Res 2(1):20–25

    Google Scholar 

  • Wang Y, Zhang X, Qiu D, Li Y, Yao L, Duan J (2018) Ultrasonic assisted microwave synthesis of poly (chitosan-co-gelatin)/polyvinyl pyrrolidone IPN hydrogel. Ultrason Sonochem 40:714–719

    Article  CAS  PubMed  Google Scholar 

  • Wei L, Zhaoyang L, Wenshen L, Feng X-D (1993) Chemical modification of biopolymers-mechanism of model graft copolymerization of chitosan. J Biomater Sci Polym Ed 4(5):557–566

    Article  Google Scholar 

  • Wu D (2017) Synthesis and characterization of O-carboxymethyl chitosan grafted colorants and supported catalysts. PhD thesis. Tianjin University

    Google Scholar 

  • Zargar V, Asghari M, Dashti A (2015) A review on chitin and chitosan polymers: structure, chemistry, solubility, derivatives, and applications. Chem Bio Eng Rev 2(3):204–226

    CAS  Google Scholar 

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Liu, X., Jiang, Q. (2019). Modification of Chitosan/Chitin and Its Oligosaccharides. In: Zhao, L. (eds) Oligosaccharides of Chitin and Chitosan. Springer, Singapore. https://doi.org/10.1007/978-981-13-9402-7_7

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