Chitin and Chitosan

The article contains sections titled: 1. Introduction 2. Molecular Structure and Conformation 2.1. Chitin 2.2. Chitosan 3. Raw Materials and Production 3.1. Isolation of Chitin from Crab and Shrimp Shells 3.2. Preparation of Chitosan from Chitin 4. Metabolism and Biosynthesis 5. Chemical Properties 5.1. Reactions on the Amino Group 5.1.1. N-Acylation 5.1.2. Formation of N-Alkylidene and N-Arylidene Derivatives 5.1.3. N-Alkylation and N-Arylation 5.2. Reactions at the Hydroxyl Group 5.3. Reactions at C-6 5.4. Graft Polymerization on Chitin and Chitosan 6. Application Forms and Formulations 7. Uses 8. Economic Aspects 9. Toxicology and Environmental Aspects

[1]  R. Muzzarelli,et al.  Removal of cyanide and phosphate traces from brines and sea-water on metal ion derivatives of chitosan , 1972 .

[2]  G. Roberts,et al.  Reactions of chitosan: 3. Preparation and reactivity of Schiff's base derivatives of chitosan , 1981 .

[3]  K. Liang,et al.  Adsorption of Gold(III) Ions onto Chitosan and N-Carboxymethyl Chitosan: Equilibrium Studies , 1999 .

[4]  K. Kaifu,et al.  Preparation of hexanoyl, decanoyl, and dodecanoylchitin , 1981 .

[5]  S. Tokura,et al.  Studies on Chitin. III. Preparation of Chitin Fibers , 1979 .

[6]  M. Pistonesi,et al.  Emulsification properties of chitosan , 1998 .

[7]  H. Seo,et al.  Effect of multiporous microspheres derived from chitin and partially deacetylated chitin on the activation of mouse peritoneal macrophages. , 1987, Vaccine.

[8]  K. Vårum,et al.  Quantitative studies of the binding of wheat germ agglutinin (WGA) to chitin-oligosaccharides and partially N-acetylated chitosans suggest inequivalence of binding sites , 1999 .

[9]  L. Hall,et al.  Ultrastructure of chitosan and some gel‐forming, branched‐chain chitosan derivatives , 1981 .

[10]  H. Inui,et al.  Calcium chloride as a biomimetic intermediate for the mineralization of carbonate ions of water as calcium carbonate in gelatinous matrices of chitosan and chitin , 1997 .

[11]  R. Duncan,et al.  Potential of low molecular mass chitosan as a DNA delivery system: biocompatibility, body distribution and ability to complex and protect DNA. , 1999, International journal of pharmaceutics.

[12]  Y Ikada,et al.  In vitro and in vivo degradation of films of chitin and its deacetylated derivatives. , 1997, Biomaterials.

[13]  S. Aiba.  Studies on chitosan: 3. Evidence for the presence of random and block copolymer structures in partially N-acetylated chitosans. , 1991, International journal of biological macromolecules.

[14]  M. Rinaudo,et al.  New method for the quaternization of chitosan , 1986 .

[15]  A. Arof,et al.  Chitosan–lithium triflate electrolyte in secondary lithium cells , 1999 .

[16]  O. Smidsrod,et al.  Determination of the degree of N-acetylation and the distribution of N-acetyl groups in partially N-deacetylated chitins (chitosans) by high-field n.m.r. spectroscopy. , 1991, Carbohydrate research.

[17]  O. Smidsrod,et al.  13C-n.m.r. studies of the acetylation sequences in partially N-deacetylated chitins (chitosans). , 1991, Carbohydrate research.

[18]  A. Hoekstra,et al.  Percutaneous microcrystalline chitosan application for sealing arterial puncture sites. , 1998, Biomaterials.

[19]  S. Lin,et al.  Novel method for the preparation of controlled-release theophylline granules coated with a polyelectrolyte complex of sodium polyphosphate-chitosan. , 1985, Journal of pharmaceutical sciences.

[20]  J. Arul,et al.  Chitosan Coating Effect on Storability and Quality of Fresh Strawberries , 1991 .

[21]  M. L. Huguet,et al.  Calcium alginate beads coated with chitosan: Effect of the structure of encapsulated materials on their release , 1996 .

[22]  T. Uragami,et al.  Studies on syntheses and permeabilities of special polymer membranes: 35. Preparation and permeation characteristics of chitin membranes , 1981 .

[23]  R. Muzzarelli,et al.  Preparation and characterization of ampicillin loaded methylpyrrolidinone chitosan and chitosan microspheres. , 1998, Biomaterials.

[24]  F. Tanfani,et al.  The N-permethylation of chitosan and the preparation of N-trimethyl chitosan iodide , 1985 .

[25]  S. Hirano,et al.  N-acetylation in chitosan and the rate of its enzymic hydrolysis. , 1989, Biomaterials.

[26]  Y. Kikuchi.  Polyelectrolyte complex of heparin with chitosan , 1974 .

[27]  D. Horton,et al.  Preparation from chitin of (1-4)-2-amino-2-deoxy-beta-D-glucopyranuronan and its 2-sulfoamino analog having blood-anticoagulant properties. , 1973, Carbohydrate research.

[28]  T. Hsien,et al.  Heterogeneous Cross-Linking of Chitosan Gel Beads: Kinetics, Modeling, and Influence on Cadmium Ion Adsorption Capacity , 1997 .

[29]  L. Hall,et al.  SYNTHESIS OF FLUORESCENT PROBE ‐ CARBOHYDRATE CONJUGATES , 1981 .

[30]  N. Matsuda,et al.  Some N-arylidenechitosan gels , 1979 .

[31]  S. Hirano,et al.  The effect of N-substitution on the hydrolysis of chitosan by an endo-chitosanase , 1995 .

[32]  Kew-Ho Lee,et al.  Chitosan membranes crosslinked with sulfosuccinic acid for the pervaporation separation of water/alcohol mixtures , 1999 .

[33]  S. Hirano.  A Facile Method for the Preparation of Novel Membranes from N-Acyl- and N-Arylidene-chitosan Gels , 1978 .

[34]  N. Benhamou,et al.  Ultrastructural and cytochemical aspects of the effect of chitosan on decay of bell pepper fruit , 1994 .

[35]  Kozo Nakamura,et al.  Development of a model for analyzing the swelling rate of ionic gels on the basis of the diffusion of mobile ions : Application to the pH-sensitive swelling of a polyelectrolyte complex gel prepared from xanthan and chitosan , 1996 .

[36]  O. Damour,et al.  Chitosan-chondroitin sulfate and chitosan-hyaluronate polyelectrolyte complexes: biological properties. , 1998, Biomaterials.

[37]  Y. Yagi,et al.  Periodate oxidation of the non-reducing end-groups of substrates increases the rates of enzymic hydrolyses by chitinase and by lysozyme , 1981 .

[38]  J. V. Alstine,et al.  Synthesis and characterization of poly(ethylene glycol) derivatives , 1984 .

[39]  Y. Koyama,et al.  Studies on chitin. 13. New polysaccharide/polypeptide hybrid materials based on chitin and poly(.gamma.-methyl L-glutamate) , 1988 .

[40]  E. Ruckenstein,et al.  Albumin separation with Cibacron Blue carrying macroporous chitosan and chitin affinity membranes , 1998 .

[41]  K. Vårum,et al.  Mode of action of chitin deacetylase from Mucor rouxii on partially N-acetylated chitosans , 1998 .

[42]  San-Lang Wang,et al.  Deproteinization of Shrimp and Crab Shell with the Protease of Pseudomonas Aeruginosa K-187 , 1998 .

[43]  F. Mi,et al.  Sustained-release of oxytetracycline from chitosan microspheres prepared by interfacial acylation and spray hardening methods. , 1997, Journal of microencapsulation.

[44]  Changzhi Zhao,et al.  Electrochemiluminescence Sensor Having a Pt Electrode Coated with a Ru(bpy)^3^2+-Modified Chitosan/Silica Gel Membrane , 1998 .

[45]  T. Yoshioka,et al.  Encapsulation of mammalian cell with chitosan‐CMC capsule , 1990, Biotechnology and bioengineering.

[46]  S. Tokura,et al.  Studies on Chitin. I. Acetylation of Chitin , 1979 .

[47]  Shiro Kobayashi,et al.  Determination of the degree of acetylation of chitin/chitosan by pyrolysis-gas chromatography in the presence of oxalic Acid. , 1998, Analytical chemistry.

[48]  S. Hirano,et al.  Absence of a hypocholesterolaemic action of chitosan in high-serum-cholesterol rabbits , 1995 .

[49]  J. Sugiyama,et al.  Structural study of α chitin from the grasping spines of the arrow worm ( Sagitta spp. ) , 1995 .

[50]  F. Tanfani,et al.  N-(carboxymethylidene)chitosans and N-(carboxymethyl)chitosans: Novel chelating polyampholytes obtained from chitosan glyoxylate , 1982 .

[51]  M Suzuki,et al.  Antitumor effect of hexa-N-acetylchitohexaose and chitohexaose. , 1986, Carbohydrate research.

[52]  J. Blackwell,et al.  The structure of ?-chitin , 1978 .

[53]  Robert Y. M. Huang,et al.  Pervaporation with chitosan membranes II. Blend membranes of chitosan and polyacrylic acid and comparison of homogeneous and composite membrane based on polyelectrolyte complexes of chitosan and polyacrylic acid for the separation of ethanol-water mixtures , 1997 .

[54]  S. Hirano,et al.  Formatoin of the polyelectrolyte complexes of some acidic glycosaminoglycans with partially N-acylated chitosans , 1978 .

[55]  E. Kokufuta,et al.  On the salt-linkage formations of porous and nonporous silica particles with trimethylammonium glycol chitosan iodide , 1981 .

[56]  F. Tanfani,et al.  Preparation and characteristic properties of dithiocarbamate chitosan, a chelating polymer , 1982 .

[57]  A. Illanes,et al.  Reactor performance under thermal inactivation and temperature optimization with chitin-immobilized lactase , 1998 .

[58]  H. Katinger,et al.  Entrapment of animal cells for production of monoclonal antibodies and other biomolecules , 1983, Nature.

[59]  R. Marchessault,et al.  Degree of Acetylation of Chitin and Extent of Grafting PHB on Chitosan Determined by Solid State 15N NMR , 1999 .

[60]  V. Zecchi,et al.  Controlled Insulin Release from Chitosan Microparticles , 1998, Archiv der Pharmazie.

[61]  N. Tsubokawa,et al.  Grafting reaction of living polymer cations with amino groups on chitosan powder , 1998 .

[62]  F. Hoppe-Seyler.  Ueber Chitin und Cellulose , 1894 .

[63]  Y. Ohe,et al.  Selective N-acylation of chitosan. , 1976, Carbohydrate research.

[64]  T. Uragami,et al.  Studies on syntheses and permeabilities of special polymer membranes, 69. Comparison of permeation and separation characteristics for aqueous alcoholic solutions by pervaporation and new evapomeation methods through chitosan membranes , 1988 .

[65]  Atsuyoshi Nakayama,et al.  Chitosan and gelatin based edible films: state diagrams, mechanical and permeation properties , 1998 .

[66]  A. Mochizuki,et al.  Distribution of Chitinase and β-N-Acetylhexosaminidase in the Organs of a Few Squid and a Cuttlefish , 1998 .

[67]  S. Hirano,et al.  Chitosan: A Biocompatible Material for Oral and Intravenous Administrations , 1990 .

[68]  S. Tokura,et al.  Endothelial cell responses to chitin and its derivatives. , 1998, Journal of biomedical materials research.

[69]  S. Hirano,et al.  N-Lower-fatty-acyl Derivatives of Chitosan as Adsorbents for Lysozyme and Chitinase , 1991 .

[70]  M. Alonso,et al.  Evaluation of cationic polymer-coated nanocapsules as ocular drug carriers , 1997 .

[71]  S. Nishimura,et al.  Studies on Chitin. VII. Preparations of p-Substituted Benzoylchitins , 1982 .

[72]  J. Iida,et al.  Stimulation of non-specific host resistance against Sendai virus and Escherichia coli infections by chitin derivatives in mice. , 1987, Vaccine.

[73]  S. Nishimura,et al.  Introduction of poly(L‐alanine) side chains into chitin as versatile spacer arms having a terminal free amino group and immobilization of nadh active sites , 1992 .

[74]  Gyoujin Cho,et al.  Preparation and Characterization of α-Amylase Immobilized Inorganic/Organic Hybrid Membrane Using Chitosan as a Dispersant in the Sol-Gel Process , 1997 .

[75]  S. Nishimura,et al.  Preparation of Chitin/Polystyrene Hybrid Materials by Efficient Graft Copolymerization Based on Mercaptochitin , 1996 .

[76]  K. Tokuyasu,et al.  Purification and characterization of extracellular chin deacetylase from Colletotrichum lindemuthianum. , 1996, Bioscience, biotechnology, and biochemistry.

[77]  H. Terayama.  Method of colloid titration (a new titration between polymer ions) , 1952 .

[78]  Anthony L. Andrady,et al.  Elastic behavior of chitosan films , 1997 .

[79]  Hwai‐Shen Liu,et al.  Immobilization of isoamylase on carboxymethyl-cellulose and chitin , 1997 .

[80]  H. Minamisawa,et al.  Adsorption behavior of cobalt(II) on chitosan and its determination by tungsten metal furnace atomic absorption spectrometry , 1999 .

[81]  R. Muzzarelli,et al.  Glutamate glucan and aminogluconate glucan, new chelating polyampholytes obtained from chitosan , 1986 .

[82]  H. Inui,et al.  Chitosan-calcium carbonate composites: Biomimetic mineralization of aqueous carbonate ions into chitosan-ca1cium alginate hydrogels , 1998 .

[83]  Y. Adachi,et al.  Adsorption of Metal Ions on a New Chelating Ion-Exchange Resin Chemically Derived from Chitosan , 1991 .

[84]  G. Roberts,et al.  Reactions of chitosan: 4. Preparation of organosoluble derivatives of chitosan , 1982 .

[85]  Y. Lee,et al.  Pervaporation of ionically surface crosslinked chitosan composite membranes for water-alcohol mixtures , 1997 .

[86]  E. Ruckenstein,et al.  Cross-linked macroporous chitosan anion-exchange membranes for protein separations , 1998 .

[87]  J. Dutkiewicz.  Some aspects of the reaction between chitosan and formaldehyde , 1983 .

[88]  A. Ito,et al.  Permeability of CO2 through chitosan membrane swollen by water vapor in feed gas , 1997 .

[89]  G. Roberts,et al.  Evaluation of infrared spectroscopic techniques for analysing chitosan , 1985 .

[90]  L. Vachoud,et al.  Formation and characterisation of a physical chitin gel , 1997 .

[91]  K. Kurita.  Reactivity characteristic of squid β-chitin as compared with those of shrimp chitin : high potentials of squid chitin as a starting material for facile chemical modifications , 1994 .

[92]  M. Nakajima,et al.  DEVELOPMENT OF ABSORBABLE SUTURES FROM CHITIN1 , 1984 .

[93]  S. Hirano,et al.  Biological Gels: The Gelation of Chitosan and Chitin , 1991 .

[94]  R. Muzzarelli,et al.  Immobilized enzymes on chitosan columns: α‐Chymotrypsin and acid phosphatase , 1976 .

[95]  S. Nishimura,et al.  Cationic and radical graft copolymerization of styrene onto iodochitin , 1992 .

[96]  S. Hirano,et al.  Incorporation of Glucoamylase into Some Polyelectrolyte Complexes , 1978 .

[97]  Cenk Aral,et al.  Alternative approach to the preparation of chitosan beads , 1998 .

[98]  K. Kurita,et al.  Studies on chitin, 3. Preparation of pure chitin, poly(N‐acetyl‐D‐glucosamine), from the water‐soluble chitin , 1977 .

[99]  M. Miles,et al.  X-ray fibre diffraction studies of chitosan and chitosan gels , 1992 .

[100]  Y. Ohe,et al.  Chitosan gel: a novel polysaccharide gel , 1975 .

[101]  K. Kurita,et al.  Studies on chitin: 17. Introduction of long alkylidene groups and the influence on the properties , 1988 .

[102]  S. Hirano,et al.  SEM ultrastructure studies of N-acyl- and N-benzylidene-chitosan and chitosan membranes. , 1981, Journal of biomedical materials research.

[103]  San-Lang Wang,et al.  Original PapersReversible Immobilization of Chitinase via Coupling to Reversibly Soluble Polymer , 1998 .

[104]  N. Matsuda,et al.  Permeability properties of gels and membranes derived from chitosan. , 1980, Journal of biomedical materials research.

[105]  M Suzuki,et al.  Protecting Effect of Chitin and Chitosan on Experimentally Induced Murine Candidiasis , 1984, Microbiology and immunology.

[106]  F. Tanfani,et al.  N-(o-carboxybenzyl) chitosans: Novel chelating polyampholytes , 1982 .

[107]  K. Kurita,et al.  Studies on chitin, 1. Solubility change by alkaline treatment and film casting , 1975 .

[108]  F. Tanfani,et al.  The characterization of N-methyl, N-ethyl, N-propyl, N-butyl and N-hexyl chitosans, novel film-forming polymers , 1983 .

[109]  S. Suzuki,et al.  Protective Effect of N‐Acetyl Chitohexaose on Listeria monocytogenes Infection in Mice , 1989, Microbiology and immunology.

[110]  S. Hirano,et al.  Some O-Stearoyl Derivatives of Chitosan Prepared via Its Schiff’s Base Intermediates , 1983 .

[111]  F. Omil,et al.  Protein recovery during the overall treatment of wastewaters from fish-meal factories , 1998 .

[112]  K. Naka,et al.  Chitin-graft-poly(2-methyl-2-oxazoline) enhanced solubility and activity of catalase in organic solvent. , 1998, International journal of biological macromolecules.

[113]  Y. Kikuchi,et al.  Polyelectrolyte complexes of sodium dextran sulfate with chitosan, 2 , 1977 .

[114]  Y. Okamoto,et al.  Chitin and chitosan activate complement via the alternative pathway , 1998 .

[115]  C. McCormick,et al.  Homogeneous solution reactions of cellulose, chitin, and other polysaccharides to produce controlled‐activity pesticide systems , 1979 .

[116]  Ken-ichiro Hayashi,et al.  Cosmetic and Pharmaceutical Uses of Chitin and Chitosan , 1991 .

[117]  T. Miller,et al.  Dietary chitosan inhibits hypercholesterolaemia and atherogenesis in the apolipoprotein E-deficient mouse model of atherosclerosis. , 1998, Atherosclerosis.

[118]  V. Zecchi,et al.  Chitosan microcapsules as controlled release systems for insulin. , 1997, Journal of microencapsulation.

[119]  N. Matsuda,et al.  N-Methylenechitosan gels, and some of their properties as media for gel chromatography☆ , 1979 .

[120]  Y. Yagi,et al.  The effects of N-substitution of chitosan and the physical form of the products on the rate of hydrolysis by chitinase from Streptomyces griseus. , 1980, Carbohydrate research.

[121]  M. Noda,et al.  Preparation of poly(acyl)chitosans , 1980 .