Determination of the degree of N-acetylation for chitin and chitosan by various NMR spectroscopy techniques: A review

Carbohydrate Polymers

Volumn 79, Issue 4, 2010, Pages 801-810

  Kasaai, Mohammad R ^a  

^a SARI AGRICULTURAL SCIENCES AND NATURAL RESOURCES UNIVERSITY   (Iran)

Author keywords

13C NMR; 15N NMR; 1H NMR; Chitin; Chitosan; Degree of N acetylation

Indexed keywords

APPROPRIATE TECHNIQUES; CHITIN-CHITOSAN; N-ACETYLATION; NMR SPECTROSCOPY; NMR TECHNIQUES;

ACETYLATION; BIOPOLYMERS; CHITIN; CHITOSAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; RESONANCE;

NUCLEAR MAGNETIC RESONANCE;

EID: 73849103183     PISSN: 01448617     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carbpol.2009.10.051     Document Type: Review

References (84)

1. Aiba S. Studies on chitosan: 1, Determination of the degree of N -acetylation of chitosan by ultraviolet spectrophotometry and gel permeation chromatography. International Journal of Biological Macromolecules 8 (1986) 173-176
2. Allan C.R., and Hadwiger L.A. The fungicidal effect of chitosan on fungi of varying cell wall composition. Experimental Mycology 3 (1979) 285-287
3. American Standard Test Method, ASTM International. (2003). 13.01, F2260-03. Available from http://www.astm.org.
4. Averbach B.L. Film-forming capabilities of chitosan. In: Muzzarelli R.A.A., and Pariser E.R. (Eds). Proceedings of the first international conference on chitin/chitosan (1978), MIT Press, Cambridge, MA, USA 199-209
5. Baxter A., Dillon M., Taylor K.D., and Roberts G.A.F. Improved method for IR determination of the degree of N-acetylation of chitosan. International Journal of Biological Macromolecules 14 (1992) 166-169
6. Biagini G., Muzzarelli R.A.A., Giardino R., and Castaldini C. Biological materials for wound healing. In: Bruine C.J., Sandord P.A., and Zikakis J.P. (Eds). Advances in chitin and chitosin (1992), Elsevier Applied Science, London 16-24
7. Braun S., Kalinowski H.-O., and Berger S. 100 and more basic NMR experiments: A practical course (1996), VCH, New York
8. Brugnerotto J., Lizardi J., Goyoolea F.M., Argüelles-Monal W., Desbrières J., and Rinaudo M. An infrared investigation in relation with chitin and chitosan characterization. Polymer 42 (2001) 3569-3580
9. Bush A. Polysaccharides and complex Oligosaccharides. In: Grant D.M., and Harris R.K. (Eds). Encyclopedia of nuclear magnetic resonance (1996), John Wiley & Sons, New York 3746-3750
10. Chippendale A.M. Structural determination by nuclear magnetic resonance spectroscopy. In: Trigg G.L. (Ed). Encyclopedia of Applied Physics Vol. 20 (1997), Wiley-VCH, Inc, New York 119-158
11. Colquhoun I.J., and Goodfellow B.J. Nuclear magnetic resonance spectroscopy. In: Wilson R.H. (Ed). Spectroscopic technique for food analysis (1994), VCH Publisher, Inc., New York 87-145
12. Cruz, Z., Lauzon, H. L., Olabarrieta Arboleya, J. C., Nuin, M., Amaria, F. & Martinez de Marañón, I. (2006). Impact of chitosan on growth inhibition of micro-organisms isolated from fishery products. In Presented at 10th international conference on chitin/chitosan (10 ICCC). Montpollier, France.
13. Csuk R., and Glänzer B.I. NMR spectroscopy of fluorinated monosaccharides. (Vol. 46, pp. 73-79). Advances in carbohydrate chemistry and biochemistry (1988), Academic Press, London
14. Curotto E., and Aros F. Quantitative determination of chitosan and the percentage of free amino groups. Analytical Biochemistry 211 (1993) 240-241
15. De Nooy A.E.J., Capitani D., Masci G., and Crescenzi V. Ionic polysaccharides hydrogels via the passerini and Ugi multicomponent condensations: Synthesis, behavior and solid-state NMR characterization. Bio-macromolecules 1 (2000) 259-267
16. Domard A., and Rinaudo M. Preparation and characterization of fully deacetylated chitosan. International Journal of Biological Macromolecules 5 (1983) 49-52
17. Duarte M.L., Ferreira M.C., Marvão M.R., and Rocha J. Chitin and chitosan: An optimized methodology by FTIR spectroscopy. In: Uragami T., Kurita K., and Fukamizo T. (Eds). Chitin and chitosan in life science (2001), Kodansha Scientific Ltd., Tokyo 86-89
18. 13C CP/MAS NMR spectroscopy. International Journal of Biological Macromolecules 28 (2001) 359-363
19. Duarte M.L., Ferreira M.C., Marvão M.R., and Rocha J. An optimized method to determine the degree of acetylation of chitin and chitosan by FTIR spectroscopy. International Journal of Biological Macromolecules 31 (2002) 1-8
20. El Ghaouth A., Arul J., Asselin A., and Benhamou N. Antifungal activity of chitosan on post-harvest pathogens: Induction of morphological and cytological alterations in Rhizopus stolonifer. Mycological Research 96 (1992) 769-779
21. El Ghaouth A., Arul J., Grenier J., and Asselin A. Antifungal activity of chitosan on two postharvest pathogens of strawberry fruits. Phytopathology 82 (1992) 398-402
22. El Ghaouth A., Arul J., Wilson C., and Benhamou N. Ultrastructural and biochemical aspects of the effect of chitosan on decay of bell pepper fruit. Physiological and Molecular Plant Pathology 44 (1994) 417-432
23. 1H NMR. Carbohydrate Polymers 61 (2005) 155-161
24. Freeman F. A handbook of nuclear magnetic resonance (1988), Longman scientific & Technical, UK
25. Gail F., Persson J., Sugiyama J., Vuong R., Tanner S., and Chanzy H. Β-chitin from deep sea hydrothermal vent worms. In: Brine C.J., Sanford P.A., and Zikaris J.P. (Eds). Advances in chitin and chitosan (1991), Elsevier Applied Science, London 216-224
26. Guinesi L.S., and Cavalheiro E.T.G. The use of DSC curves to determine the acetylation degree of chitin/chitosan samples. Thermochim Acta 444 (2006) 128-133
27. Harris R.K., Becker E.D., De Menezes S.M.C., Goodfellow R., and Granger P. NMR nomenclature, nuclear spin properties and conventions for chemical shifts (IUPAC recommendations). Pure and Applied Chemistry 73 (2001) 1795-1818
28. Harris R.K., Becker E.D., de Menezes S.M.C., Goodfellow R., and Granger P. NMR nomenclature: Nuclear spin properties and conventions for chemical shifts (IUPAC recommendations). Magnetic Resonance in Chemistry 40 (2002) 489-505
29. Heux L., Brugnerotto J., Desbrie'res J., Versali M.-F., and Rinaudo M. Solid state NMR for determination of degree of acetylation of chitin and chitosan. Biomacromolecules 1 (2000) 746-751
30. 1H NMR spectroscopy. Polymer Bulletin 26 (1991) 87-94
31. Hwang K.T., Kim J.T., Jung S.T., Cho G.S., and Park H.J. Properties of chitosan-based biopolymer films with various degrees of deacetylation and molecular weights. Journal of Applied Polymer Science 89 (2003) 3476-3484
32. Kasaai M.R. A review of several reported procedures to determine the degree of N-acetylation for chitin and chitosan using infrared spectroscopy. Carbohydrate Polymers 71 (2008) 497-508
33. Kasaai M.R., Arul J., Chin S.L., and Charlet G. The use of intense femtosecond laser pulses for the fragmentation of chitosan. Journal of Photochemistry Photobiology A 120 (1999) 201-205
34. Ke H., and Chen Q. Potentiometric titration of chitosan by linear method. Huaxue Tongbao 10 (1990) 44-46
35. Kim S.S., Kim S.H., and Lee Y.M. Preparation, characterization and properties of β-chitin and N-acetylated β-chitin. Journal of Polymer Science, Part B. Polymer Physics 34 (1996) 2367-2374
36. Koenig J.L. Applications of IR spectroscopy to polymers. (pp. 77-112). Spectroscopy of polymers (1992), American Chemical Society, Washington, DC
37. Lamarque G., Viton C., and Domard A. Comparative study of the first heterogeneous deacetylation of α- and β-chitins in a multi-step process. Bio-macromolecules 5 3 (2004) 992-1001
38. Lavertu M., Xia Z., Serreqi A.N., Berrada M., Rodrrigues A., Wang D., et al. A validated H NMR method for the determination of the degree of deacetylation of chitosan. Journal of Pharmaceutical and Biomedical Analysis 32 (2003) 1149-1158
39. Mauch F., Hadwiger L.A., and Boller T. Ethylene: Symptom, not signal for the induction of chitinase and b-1-3-glucanase in pea pods by pathogens and elicitors. Plant Physiology 76 (1984) 607-611
40. Miya M., Iwamoto R., Yoshikawa S., and Mima S. I.R spectroscopic determination of CONH content in highly deacetylated chitosan. International Journal of Biological Macromolecules 2 5 (1980) 323-324
41. Muraki E., Yaku F., Iyoda J., and Kojima H. Measurement of degree of deacetylation in D-glucosamine oligosaccharides by UV absorption. Bioscience, Biotechnology, and Biochemistry 57 (1993) 1929-1930
42. Muzzarelli R.A.A. Chitin (1977), Pergamon Press Ltd., Oxford
43. Muzzarelli R.A.A., and Rocchetti R. Determination of the degree of acetylation of chitosans by first derivative ultraviolet spectrophotometry. Carbohydrate Polymers 5 (1985) 461-472
44. Muzzarelli R.A.A., Louch C., and Emanuelli M. The molecular weight of chitosans by laser light-scattering. Carbohydrate Research 164 (1987) 433-442
45. Nanjo F., Katsumi R., and Sakai K. Enzymatic method for determination of the degree of deacetylation of chiosan. Analytical Biochemistry 193 (1991) 164-167
46. Neiss T.G. Nuclear magnetic resonance instrumentation. In: Meyers John R.A. (Ed). Encyclopedia of analytical chemistry: Application, theory and instrumentation Vol. 14 (2000), John Wiley & Sons, New York 12089-12113
47. Niola F., Basora N., Chornet E., and Vidal P.F. A rapid method for the determination of the degree of N-acetylation of chitin-chitosan samples by acid hydrolysis and HPLC. Carbohydrate Research 238 (1993) 1-9
48. No H.K. Preparation and characterization of chitosan and chitosan. A Review. Journal of Aquatic Food Product Technology 4 2 (1995) 27-52
49. Olsen R., Schwartzmiller D., Weppner W., and Winandy R. Biomedical applications of chitin and its derivatives. In: Skjak-Braek G., Anthonsen T., and Sandford P. (Eds). Chitin and chitosan (1989), Elsevier Applied Science, London 813-828
50. Ottøy M.H., Värum K.M., and Smidsrød O. Compositional heterogeneity of heterogeneously deacetylated chitosans. Carbohydrate Polymers 29 1 (1996) 17-24
51. 13C-NMR spectra of sclerotized insect cuticle and of chitin. Angewande Chemie International Edition 23 (1984) 638-639
52. Prochazkova S., Värum K.M., and Østgaard K. Quantitative determination of chitosans by ninhydrin. Carbohydrate Polymers 38 (1999) 115-122
53. Rathke T.D., and Hudson S.M. Review of chitin and chitosan as fiber and film formers. Journal of macromolecule Science Review Macromolmolecule Chemical Physics C34 3 (1994) 375-437
54. Raymond L., Morin F.G., and Marchessault R.H. Degree of deacetylation of chitosan using conductometric titration and solid state NMR. Carbohydrate Research 246 (1993) 331-336
55. Rinaudo M., Le Dung P., Gey C., and Milas M. Substituent distribution on O,N-carboxymethyl chitosans by H and C NMR. International Journal of Biological Macromolecules 14 (1992) 122-128
56. Rinaudo M., Milas M., and Dung P.L. Characterization of chitosan. Influence of ionic strength and degree of acetylation on chain expansion. International Journal of Biological Macromolecules 15 (1993) 281-285
57. Rinuado M., Milas M., and Desbrières J. Characterization and solution properties of chitosan and chitosan derivatives. In: Goosen M.F.A. (Ed). Application of chitin and chitosan (1997), Technomic Publishing Co. Inc., Lancaster, PA 89-101
58. Saalwächter K., and Ramamoorthy A. Sensitivity enhancement by inverse detection in solids. In: Ramamoorthy A. (Ed). NMR of Biological Solids (2006), Taylor and Francis, Boca Raton 151-175
59. Sabins S., and Block L.H. Improved infrared spectroscopic method for the analysis of degree of N-deacetylation of chitosan. Polymer Bulletin 39 (1997) 67-71
60. 13C NMR study of chitin, chitosan and N-acylchitosans by cross polarization/magic angle spinning (CP/MAS) NMR spectroscopy. In: Hirano S., and Tokura S. (Eds). Proceedings of the second international conference on chitin and chitosan (1982), The Japanese Society of Chitin and Chitosan, Tokyo 77-81
61. 13C NMR study of chitosan and its salts with acids: Conformational characterization of polymorphs and helical structures as viewed from the conformation-dependent C Chemical shifts. Macromolecules 20 (1987) 2424-2430
62. Sandford P.A., and Hutchings G.P. Chitosan - A natural, cationic biopolymer: Commercial applications. In: Yalpani M. (Ed). Industrial polysaccharides: Genetic engineering, structure/property relations and applications (1987), Elesvier Science Publishers, Amsterdam 363-375
63. Sannan T., Kurita K., Ogura K., and Iwakura Y. Studies on chitin: (7) IR spectroscopic determination of degree of deacetylation. Polymer 19 (1978) 458-459
64. Sato H., Mizutani S.-I., Tsuge S., Ohtani H., Aoi K., Takasu A., et al. Determination of the degree of acetylation of chitin/chitosan by pyrolysis-gas chromatography in the presence of oxalic acid. Analytical Chemistry 70 (1998) 7-12
65. Schanzenbach D., and Peter M.G. NMR spectroscopy of chito-oligosaccharides. In: Muzzarelli R.A.A., and Peter M.G. (Eds). Chitin handbook (1997), European Chin Society, Atec, Grottammate 199-204
66. Shigemasa Y., Matsuura H., Sashiwa H., and Saimato H. An improved IR spectroscopic determination of degree of deacetylation of chitin. In: Domard A., Jeuniaux C., Muzzarelli R.A.A., and Roberts G.A.F. (Eds). Advances in chitin science Vol. 1 (1996), André Publisher, Lyon 204-209
67. Shigemasa Y., Matsuura H., Sashiwa H., and Saimato H. Evaluation of different absorbance ratios from infrared spectroscopy for analyzing the degree of deacetylation in chitin. International Journal of Biological Macromolecules 18 (1996) 237-242
68. Signini R., and Campana-Fitho S.P. On the preparation and characterization of chitosan hydrochloride. Polymer Bulletin 42 2 (1999) 159-166
69. 2NAc-LiCl by gel permeation chromatography. Carbohydrate Research 267 (1995) 271-290
70. Sudarshan N.R., Hoover D.G., and Knorr D. Antibacterial action of chitosan. Food Biotechnology 6 (1992) 257-272
71. Sugano M., Watanabe S., Kishi A., Izume M., and Ohtakara A. Hypocholestrolemic action of chitosans with different viscosity in rats. Lipids 23 (1998) 187-191
72. Tan S.C., Khor E., Tan T.K., and Wong S.M. The degree of deacetylation of chitosan: Advocating the first derivative UV spectrophotometry method of determination. Talanta 45 (1998) 713-719
73. Tanner S.F., Chanzy H., Vincendon M., Roux J.C., and Gaill F. High-resolution solid-state carbon-13 nuclear magnetic resonance study of chin. Macromolecules 23 (1990) 3576-3583
74. Tasi G.J., and Su W.H. Antibacterial property of shrimp chitosan against Escherichia coli. Journal of Food Protection 62 (1999) 239-243
75. Teng Q. Structural biology: Practical NMR applications. ((pp. 1-54)) (2005), Springer, New York
76. Terayama H. Method of colloid titration (a new titration between polymer ions). Journal of Polymer Science 8 (1952) 243-253
77. Tolaimate A., Desbrières J., Rhazi M., Alagui A., Vincendon M., and Vottero P. 0n the influence of deacetylation process on the physicochemical characteristics of chitosan from squid chitin. Polymer 41 (2000) 2463-2469
78. Värum K.M., Anthonsen M.W., Grasdalen H., and Smidrød O. Determination of the degree of N-acetylation and the distribution of N-acetyl groups in partially N-deacetylated chitins (chitosans) by high-field NMR spectroscopy. Carbohydrate Research 211 (1991) 17-23
79. 13C NMR studies of the acetylation sequences in partially N-acetylated chitins (chitosans). Carbohydrate Research 217 (1991) 19-27
80. Vincendon M. NMR conformational analysis of chitin in lithium chloride solution. In: Muzzarelli R.A.A., Jeuniaux C., and Gooday G.M. (Eds). Chitin in nature and technology (1985), Plenum Press, New York 343-345
81. Webb G.A. Nitrogen NMR. In: Lindon J.C., Tranter G.E., and Holmes J.L. (Eds). Encyclopedia of spectroscopy and spectrometry (2000), Academic Press, New York 1504-1514
82. Yang B.Y., and Montgomery R. Degree of acetylation of heteropolysaccharides. Carbohydrate Research 323 (2000) 156-162
83. 2-sacvenging activity of chitosan and its metal complexes. Chinese Journal of Applied Chemistry 19 (2002) 325-328
84. 15N NMR. Macromolecules 32 (1999) 518-520