Marine Biotechnology

, 8:203

Chitin and Chitosan: Functional Biopolymers from Marine Crustaceans



Chitin and chitosan, typical marine polysaccharides as well as abundant biomass resources, are attracting a great deal of attention because of their distinctive biological and physicochemical characteristics. To fully explore the high potential of these specialty biopolymers, basic and application researches are being made extensively. This review deals with the fundamental aspects of chitin and chitosan such as the preparation of chitin and chitosan, crystallography, extent of N-acetylation, and some properties. Recent progress of their chemistry is then discussed, focusing on elemental modification reactions including acylation, alkylation, Schiff base formation and reductive alkylation, carboxyalkylation, phthaloylation, silylation, tosylation, quaternary salt formation, and sulfation and thiolation.


Chitin polysaccharide marine biopolymers biomass resource biological activity chemical modification chitosan biomedical application unutilized biomass resource 


  1. Allan, CR, Hadwiger, LE 1979The fungicidal effect of chitosan on fungi of varying cell wall compositionExp Mycol3285287Google Scholar
  2. Auzély-Velty, R, Rinaudo, M 2001Chitosan derivatives bearing pendant cyclodextrin cavities: synthesis and inclusion performanceMacromolecules3435743580Google Scholar
  3. Auzély-Velty, R, Rinaudo, M 2002New supramolecular assemblies of a cyclodextrin-grafted chitosan through specific complexationMacromolecules3579557962Google Scholar
  4. Baba Y, Hirakawa H (1992) Selective adsorption of palladium(II), platinum(IV), and mercury(II) on a new chitosan derivative possessing pyridyl group. Chem Lett 1905–1908Google Scholar
  5. Baba, Y, Matsumura, N, Shiomori, K, Kawano, Y 1998Selective adsorption of mercury(II) on chitosan derivatives from hydrochloric acidAnal Sci14687690Google Scholar
  6. Badawy, MEI, Rabea, EI, Rogge, TM, Stevens, CV, Smagghe, G, Steurbaut, W, Höfte, M 2004Synthesis and fungicidal activity of new N,O-acyl chitosan derivativesBiomacromolecules5589595Google Scholar
  7. Bade, MF 1997

    Structure and isolation of native animal chitins

    Goosen, MFA eds. Applications of Chitin and ChitosanTechnomic PublishingLancaster, PA255277
    Google Scholar
  8. Biagini, G, Bertani, A, Muzarelli, RAA, Damadei, A, Benedetto, G, Belligolli, A, Riccoti, G, Zucchini, C, Rizzoli, C 1991Wound management with N-carboxybutyl chitosanBiomaterials12281286Google Scholar
  9. Blackwell, J 1969Structure of β-chitin or parallel chain systems of poly-β-(1→4)-N-acetyl-D-glucosamineBiopolymers7281298Google Scholar
  10. Blackwell, J, Gardner, KH, Kolpak, FJ, Minke, R, Classey, WB 1980Refinement of cellulose and chitin structuresACS Symp Ser141315334CrossRefGoogle Scholar
  11. Boucher, IJamieson, KRetnakaran, A eds. 2004Advances in Chitin Science, Vol. 79th ICCCMontrealGoogle Scholar
  12. Danielsen, S, Vårum, KM, Stokke, B 2004Structural analysis of chitosan mediated DNA condensation by AFM: influence of chitosan molecular parametersBiomacromolecules5928936Google Scholar
  13. Degim, Z, Celebi, N, Sayan, H, Babul, A, Erdogan, D, Take, G 2002An investigation on skin wound healing in mice with a taurine-chitosan gel formulationAmino Acids22187198Google Scholar
  14. Domard, A, Cartier, N 1989Glucosamine oligomers. 1. Preparation and characterizationInt J Biol Macromol11297302Google Scholar
  15. Domard, A, Rinaudo, M 1983Preparation and characterization of fully deacetylated chitosanInt J Biol Macromol54952Google Scholar
  16. Domard, A, Rinaudo, M, Terrassin, C 1986New method for the quaternisation of chitosanInt J Biol Macromol8105107Google Scholar
  17. Etienne, O, Schneider, A, Taddei, C, Richert, L, Schaaf, P, Voegel, JC, Egles, C, Picart, C 2005Degradability of polysaccharides multilayer films on the oral environment: an in vivo and in vitro studyBiomacromolecules6726733Google Scholar
  18. Freepons, D 1997

    Enhancing food production with chitosan seed-coating technology

    Goosen, MFA eds. Applications of Chitin and ChitosanTechnomic PublishingLancaster, PA129139
    Google Scholar
  19. Fujii, S, Kumagai, H, Noda, M 1980Preparation of poly(acyl) chitosansCarbohydr Res83389393Google Scholar
  20. Gaill, F, Persson, J, Sugiyama, J, Vuong, R, Chanzy, H 1992The chitin system in the tubes of deep-sea hydrothermal vent wormsJ Struct Biol109116128Google Scholar
  21. Gardner, KH, Blackwell, J 1975Refinement of the structure or β-chitinBiopolymers1415811595Google Scholar
  22. Goosen, MFA eds. 1997Applications of Chitin and ChitosanTechnomic PublishingLancaster, PAGoogle Scholar
  23. Hadwiger, LA, Fristensky, B, Riggleman, RC 1984

    Chitosan, a natural regulator in plant-fungal pathogen interactions, increases crop yields

    Zikakis, JP eds. Chitin, Chitosan, and Related EnzymesAcademic PressOrlando, FL291302
    Google Scholar
  24. Hall LD, Holme KR (1986) Tailored-rheology: chitosan derivatives with branched pendant sugar chains. J Chem Soc Chem Commun 217–218Google Scholar
  25. Hall LD, Yalpani M (1980) Formation of branched-chain, soluble polysaccharides from chitosan. J Chem Soc Chem Commun 1153–1154Google Scholar
  26. Harmon, RE, De, KK, Gupta, SK 1973New procedure for preparing trimethylsilyl derivatives of polysaccharidesCarbohydr Res31407409Google Scholar
  27. Hirai, A, Odani, H, Nakajima, A 1991Determination of degree of deacetylation of chitosan by 1HNMR spectroscopyPolym Bull268794Google Scholar
  28. Hirano, S 1978N-Acyl- and N-arylidene-chitosan gelsAgric Biol Chem4219391940Google Scholar
  29. Hirano, S, Ohe, Y 1975Selective N-acylation of chitosanAgric Biol Chem3913371338Google Scholar
  30. Hirano, S, Kondo, Y, Fujii, K 1985Preparation of acetylation derivatives of modified chito-oligosaccharides by the depolymerisation of partially N-acetylated chitosan with nitrous acidCarbohydr Res144338341Google Scholar
  31. Hirano, S, Yamamoto, T, Hayashi, M, Nishida, T, Inui, H 1990Chitinase activity in seeds coated with chitosan derivativesAgric Biol Chem5427192720Google Scholar
  32. Hojo, K, Maeda, M, Mu, Y, Kamada, H, Tsutsumi, Y, Nishiyama, Y, Yoshikawa, T, Kurita, K, Block, LH, Mayumi, T, Kawasaki, K 2000Facile synthesis of a chitosan hybrid of a laminin-related peptide and its antimetastatic effect in miceJ Pharm Pharmacol526773Google Scholar
  33. Holappa, J, Nevalainen, T, Savolainen, J, Soininen, P, Elomaa, M, Safin, R, Suvanto, S, Pakkanen, T, Másson, M, Loftsson, T, Järvinen, T 2004Synthesis and characterization of chitosan N-betainates having various degrees of substitutionMacromolecules3727842789Google Scholar
  34. Holme, KR, Hall, LD 1991aNovel metal chelating chitosan derivative: attachment of iminodiacetate moieties via a hydrophilic spacer groupCan J Chem69585589Google Scholar
  35. Holme, KR, Hall, LD 1991bChitosan derivatives bearing C10-alkyl glycoside branches: a temperature-induced gelling polysaccharideMacromolecules2438283833Google Scholar
  36. Holme, KR, Hall, LD 1992Preparation and characterization of N-[2-(glycosyloxy)-ethyl]chitosan derivativesCarbohydr Res225291306Google Scholar
  37. Holme, KR, Hall, LD, Speers, RA, Tung, MA 1992Solution interactions and rheology of N-[2-(glycosyloxy)-ethyl]chitosan derivativesCarbohydr Res225307320Google Scholar
  38. Hu, Y, Jiang, X, Ding, Y, Ge, H, Yuan, Y, Yang, C 2002Synthesis and characterization of chitosan-poly(acrylic acid) nanoparticlesBiomaterials2331933201Google Scholar
  39. Iwasaki, M, Yamane, S, Majima, T, Kasahara, Y, Minami, A, Harada, K, Nonaka, S, Maekawa, N, Tamura, H, Tokura, S, Shiono, M, Monde, K, Nishimura, S 2004Feasibility of polysaccharide hybrid materials for scaffolds in cartilage tissue engineering: evaluation of chondrocyte adhesion to polyion complex fibers prepared from alginate and chitosanBiomacromolecules5828833Google Scholar
  40. Izume, M, Ohtakara, A 1987Preparation of D-glucosamine oligosaccharides by the enzymatic hydrolysis of chitosanAgric Biol Chem5111891191Google Scholar
  41. Japanese Society for Chitin and Chitosan eds. 1988Kichin Kitosan (Chitin and Chitosan)Gihodo ShuppanTokyo(in Japanese)Google Scholar
  42. Japanese Society for Chitin and Chitosan eds. 1990Kichin Kitosan no Ouyou (Applications of Chitin and Chitosan)Gihodo ShuppanTokyo(in Japanese)Google Scholar
  43. Japanese Society for Chitin and Chitosan eds. 1991Kichin Kitosan Jikken Manyuaru (Experimental Manuals for Chitin and Chitosan)Gihodo ShuppanTokyo(in Japanese)Google Scholar
  44. Japanese Society for Chitin and Chitosan eds. 1995Kichin Kitosan Handobukku (Chitin and Chitosan Handbook)Gihodo ShuppanTokyo(in Japanese)Google Scholar
  45. Köpping-Höggård, K, Mel'nikova, YS, Vårum, KM, Lindman, B, Artursson, P 2003Relationship between the physical shape and the efficiency of oligomeric chitosan as a gene delivery system in vitro and in vivoJ Gene Med5130141Google Scholar
  46. Kurita, K 1994

    Facile chemical modifications of chitin utilizing soluble precursors

    Alexander, JCMenon, J eds. Trends in Macromolecules Research, Vol. 1Research TrendsTrivandrum109120
    Google Scholar
  47. Kurita, K 1996

    Chitin and chitosan, graft copolymers

    Salamone, JC eds. Polymeric Materials EncyclopediaCRC PressBoca Raton, FL12051208
    Google Scholar
  48. Kurita, K 1997a

    Chitin and chitosan derivatives

    Arshady, R eds. Desk Reference of Functional Polymers: Syntheses and ApplicationsAmerican Chemical SocietyWashington, D.C.239259
    Google Scholar
  49. Kurita, K 1997b

    Soluble precursors for efficient chemical modifications

    Goosen, MFA eds. Applications of Chitin and ChitosanTechnomic PublishingLancaster, PA103112
    Google Scholar
  50. Kurita, K 1997c

    β-Chitin and the reactivity characteristics

    Goosen, MFA eds. Applications of Chitin and ChitosanTechnomic PublishingLancaster, PA7987
    Google Scholar
  51. Kurita, K 1997d

    Preparation of squid β-chitin

    Muzzarelli, RAAPeter, MG eds. Chitin HandbookAtec EdizioniGrottammare491493
    Google Scholar
  52. Kurita, K 2001Controlled functionalization of the polysaccharide chitinProg Polym Sci2619211971Google Scholar
  53. Kurita, K, Sannan, T, Iwakura, Y 1977Preparation of pure chitin, poly(N-acetyl-d-glucosamine), from the water-soluble chitinMakromol Chem17825952602Google Scholar
  54. Kurita, K, Sannan, T, Iwakura, Y 1979Studies on chitin. VI. Binding of metal cationsJ Appl Polym Sci23511515Google Scholar
  55. Kurita, K, Ichikawa, H, Ishizeki, S, Fujisaki, H, Iwakura, Y 1982Modification reaction of chitin in highly swollen state with aromatic cyclic carboxylic acid anhydridesMakromol Chem18311611169Google Scholar
  56. Kurita, K, Ishiguro, M, Kitajima, T 1988aStudies on chitin. 17. Introduction of long alkylidene groups and the influence on the propertiesInt J Biol Macromol10124125Google Scholar
  57. Kurita, K, Yoshida, A, Koyama, Y 1988bNew polysaccharide/polypeptide hybrid materials based on chitin and poly(γ-methyl L-glutamate)Macromolecules2115791583Google Scholar
  58. Kurita, K, Inoue, S, Koyama, Y, Nishimura, S 1990(Diethylamino)ethyl)chitins: preparation and properties of novel aminated chitin derivativesMacromolecules2328652869Google Scholar
  59. Kurita, K, Inoue, S, Nishimura, S 1991aPreparation of soluble chitin derivatives as reactive precursors for controlled modifications: tosyl- and iodo-chitinsJ Polym Sci Pt A Polym Chem29937939Google Scholar
  60. Kurita, K, Kamiya, M, Nishimura, S 1991bSolubilization of a rigid polysaccharide: controlled partial N-acetylation of chitosan to develop solubilityCarbohydr Polym168392Google Scholar
  61. Kurita, K, Yoshino, H, Yokota, K, Ando, M, Inoue, S, Ishii, S, Nishimura, S 1992Preparation of tosylchitins as precursors for facile chemical modifications of chitinMacromolecules2537863790Google Scholar
  62. Kurita, K, Tomita, K, Tada, T, Ishii, S, Nishimura, S, Shimoda, K 1993aSquid chitin as a potential alternative chitin source: deacetylation behavior and characteristic propertiesJ Polym Sci Pt A Polym Chem31485491Google Scholar
  63. Kurita, K, Tomita, K, Ishii, S, Nishimura, S, Shimoda, K 1993bβ-Chitin as a convenient starting material for acetolysis for efficient preparation of N-acetylchitooligosaccharidesJ Polym Sci Pt A Polym Chem3123932395Google Scholar
  64. Kurita, K, Yoshino, H, Nishimura, S, Ishii, S 1993cPreparation and biodegradability of chitin derivatives having mercapto groupsCarbohydr Polym20239245Google Scholar
  65. Kurita, K, Ishii, S, Tomita, K, Nishimura, S, Shimoda, K 1994Reactivity characteristics of squid β-chitin as compared with those of shrimp chitin: high potentials of squid chitin as a starting material for facile chemical modificationsJ Polym Sci Pt A Polym Chem3210271032Google Scholar
  66. Kurita, K, Hashimoto, S, Yoshino, H, Ishii, S, Nishimura, S 1996Preparation of chitin/polystyrene hybrid materials by efficient graft copolymerization based on mercaptochitinMacromolecules2919391942Google Scholar
  67. Kurita, K, Akao, H, Kobayashi, M, Mori, T, Nishiyama, Y 1997aRegioselective introduction of β-galactoside branches into chitosan and chitinPolym Bull39543549Google Scholar
  68. Kurita, K, Yoshino, H, Nishimura, S, Ishii, S, Mori, T, Nishiyama, Y 1997bMercapto-chitins: a new type of supports for effective immobilization of acid phosphataseCarbohydr Polym32171175Google Scholar
  69. Kurita, K, Shimada, K, Nishiyama, Y, Shimojoh, M, Nishimura, S 1998Nonnatural branched polysaccharides: synthesis and properties of chitin and chitosan having α-mannoside branchesMacromolecules3147644769Google Scholar
  70. Kurita K, Hirakawa M, Nishiyama Y (1999) Silylated chitin: a new precursor for facile modifications and film casting. Chem Lett 771–772Google Scholar
  71. Kurita, K, Kojima, T, Nishiyama, Y, Shimojoh, M 2000aSynthesis and some properties of nonnatural amino polysaccharides: branched chitin and chitosanMacromolecules3347114716Google Scholar
  72. Kurita, K, Uno, M, Saito, Y, Nishiyama, Y 2000bRegioselectivity in protection of chitosan with the phthaloyl groupChitin Chitosan Res64350Google Scholar
  73. Kurita, K, Ikeda, H, Yoshida, Y, Shimojoh, M, Harata, M 2002aChemoselective protection of the amino groups of chitosan by controlled phthaloylation: facile preparation of a precursor useful for chemical modificationsBiomacromolecules314Google Scholar
  74. Kurita, K, Mori, S, Nishiyama, Y, Harata, M 2002bN-Alkylation of chitin and some characteristics of the novel derivativesPolym Bull48159166Google Scholar
  75. Kurita, K, Akao, H, Yang, J, Shimojoh, M 2003Nonnatural branched polysaccharides: synthesis and properties of chitin and chitosan having disaccharide maltose branchesBiomacromolecules412641268Google Scholar
  76. Kurita, K, Hirakawa, M, Kikuchi, S, Yamanaka, H, Yang, J 2004Trimethylsilylation of chitosan and some properties of the productCarbohydr Polym56333337Google Scholar
  77. Kurita, K, Sugita, K, Kodaira, N, Hirakawa, M, Yang, J 2005Preparation and evaluation of trimethylsilylated chitin as a versatile precursor for facile chemical modificationsBiomacromolecules614141418Google Scholar
  78. Lamarque, G, Viton, C, Domard, A 2004Comparative study of the first heterogeneous deacetylation of α- and β-chitins in a multistep processBiomacromolecules59921001Comparative study of the second and third heterogeneous deacetylations of α- and β-chitins in a multistep process. Biomacromolecules 5, 1899–1907Google Scholar
  79. Lamarque, G, Cretenet, M, Viton, C, Domard, A 2005New route of deacetylation of α- and β-chitins by means of freeze-pump out-thaw cyclesBiomacromolecules613801388Google Scholar
  80. Lang, G, Maresch, G, Birkel, S 1997a

    Hydroxyalkyl chitosans

    Muzzarelli, RAAPeter, MG eds. Chitin HandbookAtec EdizioniGrottammare6166
    Google Scholar
  81. Lang, G, Wendel, H, Birkel, S 1997b

    Quaternary chitosan salts

    Muzzarelli, RAAPeter, MG eds. Chitin HandbookAtec EdizioniGrottammare6770
    Google Scholar
  82. Lecourt, T, Sinaÿ, P, Chassenieux, C, Rinaudo, M, Auzély-Velty, R 2004Complexation between a hydrophobically modified chitosan and cyclodextrin homodimers singly or doubly connected through their primary sides: effects of their molecular architecture on the polymer properties in solutionMacromolecules3746354642Google Scholar
  83. Li, J, Revol, JF, Marchessault, RH 1997Effect of degree of deacetylation of chitin on the properties of chitin crystallitesJ Appl Polym Sci65373380Google Scholar
  84. Lim, S, Hudson, S 2003Review of chitosan and its derivatives as antimicrobial agents and their uses as textile chemicalsJ Macromol Sci Rev43223269Google Scholar
  85. Maresch, G, Clausen, T, Lang, G 1989

    Hydroxypropylation of chitosan

    Skjak-Bræk, GAnthonsen, TSandford, P eds. Chitin and ChitosanElsevierEssex389395
    Google Scholar
  86. Masuko, T, Minami, A, Iwasaki, N, Majima, T, Nishimura, S, Lee, YC 2005Thiolation of chitosan. Attachment of proteins via thioether formationBiomacromolecules6880884Google Scholar
  87. Matsuoka, K, Matsuzawa, Y, Kusano, K, Terunuma, D, Kuzuhara, H 2000An improved preparation of N,N′-diacetylchitobiose by continuous enzymatic degradation of colloidal chitin using dialysis tubing as a convenient separatorBiomacromolecules1798800Google Scholar
  88. Mazeau, K, Winter, WT, Chanzy, H 1994Molecular and crystal structure of a high temperature polymorph of chitosan from electron diffraction dataMacromolecules2776067612Google Scholar
  89. McGahren, WJ, Perkinson, GA, Growich, JA, Leese, RA, Ellestad, GA 1984Chitosan by fermentationProcess Biochem198890Google Scholar
  90. Mima, S, Miya, M, Iwamoto, R, Yoshikawa, S 1983Highly deacetylated chitosan and its propertiesJ Appl Polym Sci2819091917Google Scholar
  91. Minami, S, Okamoto, Y, Matsuhashi, A, Sashiwa, H, Saimoto, H, Shigemasa, Y, Tanigawa, T, Tanaka, Y, Tokura, S 1992

    Application of chitin and chitosan in large animal practice

    Brine, CJSandford, PAZikakis, PJ eds. Advances in Chitin and ChitosanElsevierEssex6169
    Google Scholar
  92. Minami, S, Raj, KD, Miyatake, K, Okamoto, Y, Ohta, H, Sasai, S, Shigemsa, Y 2001Biological effect of chitosan-lactose mixture and its clinical applicationChitin Chitosan Res7268272(in Japanese)Google Scholar
  93. Miyazaki, T, Matsushima, Y 1968Preparation of partially O-carboxymethylated chitin and its component 3-O- and 6-O-carboxymethyl-d-glucosamine, and the corresponding glucosaminitolsBull Chem Soc Jpn4127232726Google Scholar
  94. Moore, GK, Roberts, GAF 1980Chitosan gels, 1. Study of reaction variablesInt J Biol Macromol27377Google Scholar
  95. Moore, GK, Roberts, GAF 1982Reaction of chitosan: 4. Preparation of organosoluble derivatives of chitosanInt J Biol Macromol4246249Google Scholar
  96. Morimoto, M, Saimoto, H, Usui, H, Okamoto, Y, Minami, S, Shigemasa, Y 2001Biological activities of carbohydrate-branched chitosan derivativesBiomacromolecules211331136Google Scholar
  97. Muraki, E, Yaku, F, Kojima, H 1993Preparation and crystallization of D-glucosamine oligosaccharides with DP 6-8Carbohydr Res239227237Google Scholar
  98. Muzzarelli, RAA 1973Natural Chelating PolymersPergamon PressOxford83176Google Scholar
  99. Muzzarelli, RAA 1977ChitinPergamon PressOxfordGoogle Scholar
  100. Muzzarelli, RAA 1986

    The chelating ability of amino acid glucans and sugar acid chitosans

    Muzzarelli, RAAJeuniaux, CGooday, GW eds. Chitin in Nature and TechnologyPlenum PressNew York321330
    Google Scholar
  101. Muzzarelli, RAA, Vincenzi, M 1997

    Chitosans as dietary food additives

    Goosen, MFA eds. Applications of Chitin and ChitosanTechnomic PublishingLancaster, PA115127
    Google Scholar
  102. Muzzarelli, RAAPeter, MG eds. 1997Chitin HandbookAtec EdizioniGrottammareGoogle Scholar
  103. Muzzarelli, RAA, Tanfani, F 1985The N-permethylation of chitosan and the preparation of N-trimethyl chitosan iodidieCarbohydr Polym5297307Google Scholar
  104. Muzzarelli, RAA, Tanfani, F, Emanuelli, M, Mariotti, S 1982N-(Carboxymethylidene) chitosans and N-(carboxymethyl) chitosans: novel chelating polyampholytes obtained from chitosan glyoxylateCarbohydr Res107199214Google Scholar
  105. Muzzarelli, RAA, Tanfani, F, Emanuelli, M, Mariotti, S 1983The characterization of N-methyl, N-ethyl, N-propyl, N-butyl, and N-hexyl chitosans, novel film-forming polymersJ Membr Sci16295308Google Scholar
  106. Muzzarelli, RAA, Wecks, M, Filippini, O, Lough, C 1989Characteristic properties of N-carboxybutyl chitosanCarbohydr Polym11307320Google Scholar
  107. Muzzarelli, RAA, Zucchini, C, Ilari, P, Pugnaloni, A, Belmonte, MM, Biagini, G, Castaldini, C 1993Osteoconductive properties of methlpyrrolidinone chitosan in an animal modelBiomaterials14925929Google Scholar
  108. Muzzarelli, RAA, Muzzarelli, C, Tarsi, R, Miliani, M, Gobbanelli, F, Cartolari, M 2001Fungistatic activity of modified chitosans against Saprolegnia parasiticaBiomacromolecules2165169Google Scholar
  109. Nagyvary, JJ, Falk, JD, Hill, ML, Schmidt, ML, Wilkins, AK, Bradbury, EL 1979The hypolipidemic activity of chitosan and other polysaccharides in ratsNutr Rep Int20677684Google Scholar
  110. Nishi, N, Noguchi, J, Tokura, S, Shiota, H 1979Studies on chitin. I. Acetylation of chitinPolym J112732Google Scholar
  111. Nishiki, M, Tojima, T, Nishi, N, Sakairi, N 2000β-Cylodextrin-linked chitosan beads: preparation and application to removal of bisphenol A from waterCarbohydr Lett46167Google Scholar
  112. Nishimura, S 2001

    Chemical biology and biomedicine: general aspects

    Fraser-Reid, BOTastuta, KThiem, J eds. Glycoscience: Chemistry and Chemical BiologySpringerNew York6
    Google Scholar
  113. Nishimura, K, Nishimura, S, Seo, H, Nishi, N, Tokura, S, Azuma, I 1987Effect of multiporous microspheres derived from chitin and partially deacetylated chitin on the activation of mouse peritoneal macrophagesVaccine5136140Google Scholar
  114. Nishimura, S, Kuzuhara, H, Takiguchi, Y, Shimahara, K 1989Peracetylated chitobiose: preparation by specific degradation of chitn, and chemical manipulationsCarbohydr Res194223231Google Scholar
  115. Nishimura S, Kohgo O, Kurita K, Vittavatvong C, Kuzuhara H (1990) Syntheses of novel chitosan derivatives soluble in organic solvents by regioselective chemical modifications. Chem Lett, 243–246Google Scholar
  116. Nishimura, S, Kohgo, O, Kurita, K, Kuzuhara, H 1991Chemospecific manipulations of a rigid polysaccharide: syntheses of novel chitosan derivatives with excellent solubility in common organic solvents by regioselective chemical modificationsMacromolecules2447454748Google Scholar
  117. Nishimura S, Miura Y, Ren L, Sato M, Yamagishi A, Nishi N, Tokura S, Kurita K, Ishii S (1993) An efficient method for the syntheses of novel amphiphilic polysaccharides by regio- and thermoselective modifications of chitosan. Chem Lett, 1623–1626Google Scholar
  118. Nishimura, S, Kai, H, Shinada, K, Yoshida, T, Tokura, S, Kurita, K, Nakashima, H, Yamamoto, N, Uryu, T 1998Regioselective syntheses of sulfated polysaccharides: specific anti-HIV-1 activity of novel chitin sulfatesCarbohydr Res306427433Google Scholar
  119. Nishiyama, Y, Yoshida, T, Mori, T, Ishii, S, Kurita, K 1998Asymmetric reduction with chitosan/dihydronicotinamide conjugates: influence of L-alanine spacer arms on reducing performanceReact Funct Polym378391Google Scholar
  120. Nishiyama, Y, Yoshikawa, T, Ohara, N, Kurita, K, Hojo, K, Kamada, H, Tsutsumi, Y, Mayumi, T, Kawasaki, K 2000A conjugate from a laminin-related peptide, Tyr-Ile-Gly-Ser-Arg, and chitosan: efficient and regioselective conjugation and significant inhibitory activity on the experimental cancer metastasisJ Chem Soc Perkin Trans111611165Google Scholar
  121. No, HK, Meyers, SP 1997

    Preparation of chitin and chitosan

    Muzzarelli, RAAPeter, MG eds. Chitin HandbookAtec EdizioniGrottammare475489
    Google Scholar
  122. Noishiki, Y, Kuga, S, Wada, M, Hori, K, Nishiyama, Y 2004Guest selectivity in complexation of β-chitinMacromolecules3768396842Google Scholar
  123. Nonaka, K, Kazama, S, Goto, A, Fukuda, H, Yoshioka, H, Yoshioka, H 2002Spin probe study on the interaction of chitosan-derived polymer surfactants with lipid membraneJ Colloid Interface Sci246288295Google Scholar
  124. Okuyama, K, Noguchi, K, Miyazawa, T, Yui, T, Ogawa, K 1997Molecular and crystal structure of hydrated chitosanMacromolecules3058495855Google Scholar
  125. Ouchi, T, Nishizawa, H, Ohya, Y 1998Aggregation phenomenon of PEG-grafted chitosan in aqueous solutionPolymer3951715175Google Scholar
  126. Philippova, OE, Volkov, EV, Sitnikova, NL, Khokhlov, AR, Desbriéres, J, Rinaudo, M 2001Two types of hydrophobic aggregates in aqueous solutions of chitosan and its hydrophobic derivativeBiomacromolecules2483490Google Scholar
  127. Rabea, EI, Badawy, MET, Stevens, CV, Smagghe, G, Steurbaut, W 2003Chitosan as antimicrobial agent: applications and mode of actionBiomacromolecules414571465Google Scholar
  128. Rinaudo, R, Desbrières, J, Dung, P, Binh, T, Dong, NT 2001NMR investigation of chitosan derivatives formed by the reaction of chitosan with levulinic acidCarbohydr Polym46339348Google Scholar
  129. Roberts, GAF 1992aChitin ChemistryMacmillanLondonGoogle Scholar
  130. Roberts, GAF 1992bChitin ChemistryMacmillanLondon206229Google Scholar
  131. Roberts, GAF 1992cChitin ChemistryMacmillanLondon229249Google Scholar
  132. Rössle, M, Flot, D, Engel, J, Burghammer, M, Riekel, C, Chanzy, H 2003Fast intracrystalline hydration of β-chitin revealed by combined microdrop generation and on-line synchrotron radiation microdiffractionBiomacromolecules4981986Google Scholar
  133. Rudall, KM, Kenchington, W 1973The chitin systemBiol Rev49597636Google Scholar
  134. Rutherford FA, Austin PR (1978). Marine chitin properties and solvents. In: Proceedings of the 1st Int. Conference on Chitin/Chitosan, Muzzarelli RAA, Pariser ER, eds. (MIT Sea Grant Report MITSG 78-7) pp 182–192Google Scholar
  135. Saito, Y, Putaux, JL, Okano, T, Gaill, F, Chanzy, H 1997Structural aspects of the swelling of β chitin in HCl and its conversion into α chitinMacromolecules3038673873Google Scholar
  136. Sandford, PA 2003

    Commercial sources of chitin and chitosan and their utilization

    Vårum, KMDomard, ASmidsrød, O eds. Advances in Chitin Science, Vol. 6NTNUTrondheim3542
    Google Scholar
  137. Sannan, T, Kurita, K, Iwakura, Y 1975Studies on chitin. 1. Solubility change by alkaline treatment and film castingMakromol Chem17611911195Google Scholar
  138. Sannan, T, Kurita, K, Iwakura, Y 1976Studies on chitin. 2. Effect of deacetylation on solubilityMakromol Chem17735893600Google Scholar
  139. Sannan, T, Kurita, K, Ogura, K, Iwakura, Y 1978Studies on chitin. 7. I.R. spectroscopic determination of degree of deacetylationPolymer19458459Google Scholar
  140. Sashiwa, H, Saimoto, H, Shigemasa, Y, Tokura, S 1993N-Acetyl group distribution in partially deacetylated chitins perpared under homogeneous conditionsCarbohydr Res242167172Google Scholar
  141. Sashiwa H, Makimura Y, Shigemasa Y, Roy R (2000) Chemical modification of chitosan: preparation of chitosan-sialic acid branched polysaccharide hybrids. Chem Commun 909–910Google Scholar
  142. Sashiwa, H, Shigemasa, Y, Roy, R 2001Highly convergent synthesis of dendrimerized chitosan-sialic acid hybridMacromolecules3432113214Synthesis of dendronized chitosan-sialic acid hybrid using convergent grafting of preassembled dendrons built on gallic acid and tri(ethylene glycol) backbone. Macromolecules 34, 3905–3909Google Scholar
  143. Sashiwa, H, Shigemasa, Y, Roy, R 2002aPreparation of chitosan-dendrimer hybrid via short spacerCarbohydr Polym47191199Google Scholar
  144. Sashiwa, H, Kawasaki, N, Nakayama, A, Muraki, E, Yamamoto, N, Zhu, H, Nagano, H, Omura, Y, Saimoto, H, Shigemasa, Y, Aiba, S 2002bSynthesis of organosoluble, palladium adsorbable, and biodegradable chitosan derivatives toward the chemical plating on plasticsBiomacromolecules311201125Google Scholar
  145. Sashiwa, H, Kawasaki, N, Nakayama, A, Muraki, E, Yamamoto, N, Aiba, S 2002cSynthesis of water-soluble chitosan derivatives by simple acetylationBiomacromolecules311261128Google Scholar
  146. Serizawa, T, Yamaguchi, M, Matsuyama, T, Akashi, M 2000Alternating bioactivity of polymeric layer-by-layer assemblies: anti- vs procoagulation of human blood on chitosan and dextran sulfate layersBiomacromolecules1306309Google Scholar
  147. Serizawa, T, Yamaguchi, M, Akashi, M 2002Alternating bioactivity of polymeric layer-by-layer assemblies: anticoagulation vs procoagulation of human bloodBiomacromolecules3724731Google Scholar
  148. Shigemasa Y, Ishida A, Sashiwa H, Saimoto H, Okamoto Y, Minami S, Matsuhashi A (1995) Synthesis of a new chitin derivative, (1-carboxyethyl)chitosan. Chem Lett 623–624Google Scholar
  149. Shimahara, K, Takiguchi, Y 1988

    Preparation of crustacean chitin

    Wood, WAKellog, ST eds. Methods in Enzymology, Vol. 161Academic PressNew York417423
    Google Scholar
  150. Shimahara, K, Takiguchi, Y, Ohkouchi, K, Kitamura, K, Okada, O 1984

    Chemical composition and some properties of custacean chitin prepared by use of proteolytic activity of Pseudomonas maltophilia LC102

    Zikakis, JP eds. Chitin, Chitosan, and Related EnzymesAcademic PressOrlando, FL239255
    Google Scholar
  151. Sugano, M, Fujikawa, T, Hiratsuji, Y, Nakashima, K, Fukuda, N, Hasegawa, Y 1980A novel use of chitosan as a hypocholesterolemic agent in ratsAm J Clin Nutr33787793Google Scholar
  152. Sugano, M, Watanabe, S, Kishi, A, Izume, M, Ohtakara, A 1988Hypocholesterolemic action of chitosans with different viscosity in ratsLipids23187191Google Scholar
  153. Sugimoto, M, Morimoto, M, Sashiwa, H, Saimoto, H, Shigemasa, Y 1998Preparation and characterization of water-soluble chitin and chitosan derivativesCarbohydr Polym364959Google Scholar
  154. Takiguchi, Y, Shimahara, K 1988N,N′-Diacetylchitobiose production from chitin by Vibrio anguillarum strain E-383aLett Appl Microbiol6129131Google Scholar
  155. Tamura, H, Hamaguchi, T, Tokura, S 2004

    Destruction of rigid crystalline strucure to prepare chitin solution

    Boucher, IJamieson, KRetnakaran, A eds. Advances in Chitin Science, Vol. 79th ICCCMontreal8487
    Google Scholar
  156. Tanida, F, Tojima, T, Han, SM, Nishi, N, Tokura, S, Sakairi, N, Seino, H, Hamada, K 1998Novel synthesis of a water-soluble cyclodextrin-polymer having a chitosan skeltonPolymer3952615263Google Scholar
  157. Thierry, B, Winnik, FM, Merhi, Y, Silver, J, Tabrizian, M 2003aBioactive coatings of endovascular stents based on polyelectrolyte multilayersBiomacromolecules415641571Google Scholar
  158. Thierry, B, Winnik, FM, Merhi, Y, Tabrizian, M 2003bNanocoatings onto arteries via layer-by-layer deposition: toward the in vivo repair of damaged blood vesselsJ Am Chem Soc12574947495Google Scholar
  159. Thome, JP, Jeuniaux, C, Weltrowski, M 1997

    Applications of chitosan for the elimination of organochlorine xenobiotics from wastewater

    Goosen, MFA eds. Applications of Chitin and ChitosanTechnomic PublishingLancaster, PA309331
    Google Scholar
  160. Tokoro, A, Suzuki, K, Matsumoto, T, Mikami, T, Suzuki, S, Suzuki, M 1988aChemotactic response of human neutrophils to N-acetyl chitohexaose in vitroMicrobiol Immunol32387395Google Scholar
  161. Tokoro, A, Tatewaki, N, Suzuki, K, Mikami, T, Suzuki, S, Suzuki, M 1988bGrowth-inhibitory effect of hexa-N-acetylchitohexaose and chitohexaose against Meth-A solid tumorChem Pharm Bull36784790Google Scholar
  162. Tokura, S, Nishi, N, Tsutsumi, A, Somorin, O 1983Studies on chitin. VIII. Some properties of water soluble chitin derivativesPolym J15485489Google Scholar
  163. Tømmeraas, K, Köping, M, Vårum, KM, Christensen, BE, Smidsrød, O 2002Preparation and characterization of chitosans with oligosaccharide branchesCarbohydr Res33724552462Google Scholar
  164. Trujillo, R 1968Preparation of carboxymethylchitinCarbohydr Res7483485Google Scholar
  165. Uchida, Y, Izume, M, Ohtakara, A 1989

    Preparation of chitosan oligomers with purified chitosanase and its application

    Skjak-Bræk, GAnthonsen, TSandford, P eds. Chitin and ChitosanElsevierEssex373382
    Google Scholar
  166. Uragami T, Tokura S, eds. (in press) Material Science of Chitin and Chitosan. (Tokyo: Kodansha Scientific).Google Scholar
  167. Uragami, TKurita, KFukamizo, T eds. 2001Chitin and Chitosan–Chitin and Chitosan in Life ScienceKodansha ScientificTokyoGoogle Scholar
  168. Usui, T, Matsui, H, Isobe, K 1990Enzymic synthesis of useful chito-oligosaccharides utilizing transglycosylation by chitinolytic enzymes in a buffer containing ammonium sulfateCarbohydr Res2036577Google Scholar
  169. Vårum, KM, Anthonsen, MW, Grasdalen, H, Smidsrød, O 1991Determination of the degree of N-acetylation and the distribution of N-acetyl groups in partially N-deacetylated chitins (chitosans) by high-field nmr spectroscopyCarbohydr Res2111723Google Scholar
  170. Vårum, KMDomard, ASmidsrød, O eds. 2003Advances in Chitin Science, Vol. 6NTNUTrondheimGoogle Scholar
  171. Yabuki, M, Uchiyama, A, Suzuki, K, Ando, A, Fujii, T 1988Purification and properties of chitosanase from Bacillus circulans MH-K1J Gen Appl Microbiol34255270Google Scholar
  172. Yalpani, M, Hall, LD 1984Some chemical and analytical aspects of polysaccharide modifications. 3. Formation of branched-chain, soluble chitosan derivativesMacromolecules17272281Google Scholar
  173. Yalpani, M, Hall, LD, Tung, MA, Brooks, DE 1983Unusual rheology of a branched, water soluble chitosan derivativeNature302812814Google Scholar
  174. Yang, J, Akao, H, Shimojoh, M, Kurita, K 2004Efficient introduction of β-maltoside branches into chitin and chitosanChitin Chitosan Res105156Google Scholar
  175. Yu, G, Morin, FG, Nobes, GAR, Marchessault, RH 1999Degree of acetylation of chitin and extent of grafting PHB in chitosan determined by solid state 15N NMRMacromolecules32518520Google Scholar
  176. Yui, T, Imada, K, Okuyama, K, Obata, Y, Suzuki, K, Ogawa, K 1994Molecular and crystal structure of the anhydrousform of chitosanMacromolecules2776017605Google Scholar
  177. Zong, Z, Kimura, Y, Takahashi, M, Yamane, H 2000Characterization of chemical and solid state structures of acylated chitosansPolymer41899906Google Scholar
  178. Zou, Y, Khor, E 2005Preparation of C-6 substituted chitin derivatives under homogeneous conditionsBiomacromolecules68087Google Scholar

Copyright information

© Springer Science+Business Media, Inc. 2006

Authors and Affiliations

  1. 1.Department of Materials and Life ScienceSeikei UniversityMusashino-shiJapan

Personalised recommendations