Bioproduction of chitooligosaccharides: Present and perspectives

Marine Drugs

Volumn 12, Issue 11, 2014, Pages 5328-5356

  Jung, Woo Jin ^a   Park, Ro Dong ^a  

^a Chonnam National University   (South Korea)

Author keywords

Bioproduction; Chemoenzymatic glycosylation; Chitin deacetylase; Chitinase; Chitooligosaccharides; Chitosanase; Enzymatic hydrolysis; Transglycosylation

Indexed keywords

BETA DEXTRO GLUCOSAMINE; CARBOHYDRATE; CHITIN; CHITIN DEACETYLASE; CHITOBIOSE; CHITOSAN; GLUCOSAMINE; MONOMER; N ACETYLGLUCOSAMINE; N,N' DIACETYLCHITOBIOSE; OLIGOSACCHARIDE; UNCLASSIFIED DRUG;

BIOTECHNOLOGICAL PRODUCTION; BIOTRANSFORMATION; CARBOHYDRATE ANALYSIS; CARBOHYDRATE METABOLISM; CARBOHYDRATE SYNTHESIS; DEACETYLATION; ENZYMATIC DEGRADATION; ENZYME REACTOR; FERMENTATION TECHNIQUE; GENETIC ENGINEERING; GLYCOSYLATION; HYDROLYSIS; MOLECULAR WEIGHT; NONHUMAN; PROTEIN ENGINEERING; REVIEW; SEPARATION TECHNIQUE; ANIMAL; CHEMISTRY; CRUSTACEA; HUMAN; METABOLISM; PROCEDURES;

CRUSTACEA; DECAPODA (CRUSTACEA);

ANIMALS; CHITIN; CHITOSAN; CRUSTACEA; HUMANS; HYDROLYSIS; OLIGOSACCHARIDES; PROTEIN ENGINEERING;

EID: 85047698587     PISSN: None     EISSN: 16603397     Source Type: Journal    
DOI: 10.3390/md12115328     Document Type: Review

References (146)

1. No, H.K.; Meyers, S.P.; Lee, K.S. Isolation and characterization of chitin from crawfish shell waste. J. Agric. Food Chem. 1989, 37, 575-579.
2. Aye, K.N.; Stevens, W.F. Technical note: Improved chitin production by pre-treatment of shrimp shells. J. Chem. Technol. Biotechnol. 2004, 79, 421-425.
3. Allan, G.G.; Fox, J.R.; Kong, N. Marine polymers, part 8. A critical evaluation of the potential sources of chitin and chitosan. In Proceeding of the 1st International Conference on Chitin/Chitosan; Muzzarelli, R.A.A., Pariser, E.R., Eds.; MIT Sea Grant: Cambridge, MA, USA, 1978; pp. 64-78.
4. Simpson, B.K.; Gagné, N.; Simpson, M.V. Bioprocessing of chitin and chitosan. In Fisheries Processing: Biotechnological Applications; Martin, A.M., Ed.; Chapman & Hall: London, UK, 1994; pp. 155-173.
5. Healy, M.G.; Romo, C.R.; Bustos, R. Bioconversion of marine crustacean shell waste. Res. Conserv. Recycl. 1994, 11, 139-147.
6. Jung, W.J.; Jo, G.Y.; Kuk, J.H.; Kim, K.Y.; Park, R.D. Extraction of chitin from red crab shell waste by cofermentation with Lactobacillus paracasei subsp. tolerans KCTC-3074 and Serratia marcescens FS-3. Appl. Microbiol. Biot. 2006, 71, 234-237.
7. Jung, W.J.; Jo, G.Y.; Kuk, J.H.; Kim, Y.J.; Oh, K.T.; Park, R.D. Production of chitin from red crab shell waste by successive fermentation with Lactobacillus paracasei KCTC-3074 and Serratia marcescens FS-3. Carbohydr. Polym. 2007, 68, 746-750.
8. Jo, G.H.; Jung, W.J.; Kuk, J.H.; Oh, K.T.; Kim, Y.J.; Park, R.D. Screening of protease-producing Serratia marcescens FS-3 and its application to deproteinization of crab shell waste for chitin extraction. Carbohydr. Polym. 2008, 74, 504-508.
9. Seyfarth, F.; Schliemann, S.; Elsner, P.; Hipler, U.C. Antifungal effect of high-and low-molecular-weight chitosan hydrochloride, carboxymethyl chitosan, chitosan oligosaccharide and N-acetyl-D-glucosamine against Candida albicans, Candida krusei and Candida glabrata. Int. J. Pharm. 2008, 353, 139-148.
10. Oliveira, E.N., Jr.; El Gueddari, N.E.; Moerschbacher, B.M.; Peter, M.G.; Franco, T.T. Growth of phytopathogenic fungi in the presence of partially acetylated chitooligosaccharides. Mycopathologia 2008, 166, 163-174.
11. Sasaki, C.; Fukamizo, T. Production of food oligosaccharides by chitinases and chitosanases: Structural biological perspective. New Food Ind. 2001, 43, 7-14.
12. Lee, H.W.; Park, Y.S.; Choi, J.W.; Yi, S.Y.; Shin, W.S. Antidiabetic effects of chitosan oligosaccharides in neonatal streptozotocin-induced noninsulin-dependent diabetes mellitus in rats. Biol. Pharm. Bull. 2003, 26, 1100-1103.
13. Xia, W.; Liu, P.; Zhang, J.; Chen, J. Biological activities of chitosan and chitooligosaccharides. Food Hydrocoll. 2011, 25, 170-179.
14. Sato, K.; Saimoto, H.; Morimoto, M.; Shigemasa, Y. Depolymerization of chitin and chitosan under hydrothermal conditions. Sen-I Gakkaishi 2003, 59, 104-109.
15. Xing, R.E.; Liu, S.; Yu, H.H.; Guo, Z.Y.; Wang, P.B.; Li, C.P.; Li, Z.; Li, P.C. Salt-assisted acid hydrolysis of chitosan to oligomers under microwave irradiation. Carbohydr. Res. 2005, 340, 2150-2153.
16. Wu, T.; Zivanovic, S.; Hayes, D.G.; Weiss, J. Efficient reduction of chitosan molecular weight by high-intensity ultrasound: Underlying mechanism and effect of process parameters. J. Agric. Food Chem. 2008, 56, 5112-5119.
17. Yoksan, R.; Akashi, M.; Miyata, M.; Chirachanchai, S. Optimal gamma-ray dose and irradiation conditions for producing low-molecular-weight chitosan that retains its chemical structure. Radiat. Res. 2004, 161, 471-480.
18. Domard, A.; Cartier, N. Glucosamine oligomers: 4. Solid state-crystallization and sustained dissolution. Int. J. Biol. Macromol. 1992, 14, 100-106.
19. Einbu, A.; Vårum, K.M. Depolymerization and de-N-acetylation of chitin oligomers in hydrochloric acid. Biomacromolecules 2007, 8, 309-314.
20. Lin, F.; Jia, X.G.; Lei, W.X.; Li, Z.J.; Zhang, T.Y. Spectra analyses of chitosans degraded by hydrogen peroxide under optimal conditions. Spectrosc. Spectr. Anal. 2009, 29, 43-47.
21. Morris, V.B.; Neethu, S.; Abraham, T.E.; Pillai, C.K.S.; Sharma, C.P. Studies on the condensation of depolymerized chitosans with DNA for preparing chitosan-DNA nanoparticles for gene delivery applications. J. Biomed. Mater. Res. Part B 2009, 89B, 282-292.
22. Jeon, Y.J.; Park, P.J.; Kim, S.K. Antimicrobial effect of chitooligosaccharides produced by bioreactor. Carbohydr. Polym. 2001, 44, 71-76.
23. Qin, C.; Zhou, B.; Zeng, L.; Zhang, Z.; Liu, Y.; Du, Y.; Xiao, L. The physicochemical properties and antitumor activity of cellulase-treated chitosan. Food Chem. 2004, 84, 107-115.
24. Aam, B.B.; Heggset, E.B.; Norberg, A.L.; Sørlie, M.; Vårum, K.M.; Eijsink, V.G.H. Production of chitooligosaccharides and their potential applications in medicine. Mar. Drugs 2010, 8, 1482-1517.
25. Lin, Y.W.; Hsiao, Y.C.; Chiang, B.H. Production of high degree polymerized chitooligosaccharides in a membrane reactor using purified chitosanase from Bacillus cereus. Food Res. Int. 2009, 42, 1355-1361.
26. Zeng, H.; Zheng, L.Y. Studies on Penicillium sp. ZDZ1 chitosanase immobilized on chitin by cross-linking reaction. Process Biochem. 2002, 38, 531-535.
27. Cantarel, B.L.; Coutinho, P.M.; Rancurel, C.; Bernard, T.; Lombard, V.; Henrissat, B. The Carbohydrate-Active enZYmes database (CAZy): An expert resource for Glycogenomics. Nucleic Acids Res. 2009, 37, D233-D238.
28. CAZy. The Carbohydrate-Active enZYmes database. Available online: http://www.cazy.org (accessed on 27 April 2010).
29. Davies, G.; Henrissat, B. Structures and mechanisms of glycosyl hydrolases. Structure 1995, 3, 853-859.
30. Henrissat, B.; Bairoch, A. Updating the sequence-based classification of glycosyl hydrolases. Biochem. J. 1996, 316, 695-696.
31. Kobayashi, S.; Kiyosada, T.; Shoda, S. Synthesis of artificial chitin: Irreversible catalytic behavior of a glycosyl hydrolase through a transition state analogue substrate. J. Am. Chem. Soc. 1996, 118, 13113-13114.
32. Sato, H.; Mizutani, S.; Tsuge, S.; Ohtani, H.; Aoi, K.; Takasu, A.; Okada, M.; Kobayashi, S.; Kiyosada, T.; Shoda, S. Determination of the degree of acetylation of chitin/chitosan by pyrolysis-gas chromatography in the presence of oxalic acid. Anal. Chem. 1998, 70, 7-12.
33. ExplorEnz-The Enzyme Database. Available online: http://www.enzyme-explorer.org/(accessed on 27 April 2010).
34. Berger, L.R.; Reynolds, D.M. The chitinase system of a strain of Streptomyces griseus. Biochem. Biophys. Acta 1958, 29, 522-534.
35. Monreal, J.; Reese, E.T. The chitinase of Serratia marcescens. J. Microbiol. 1969, 15, 689-696.
36. Sørbotten, A.; Horn, S.J.; Eijsink, V.G.; Vårum, K.M. Degradation of chitosans with chitinase B from Serratia marcescens. Production of chito-oligosaccharides and insight into enzyme processivity. FEBS J. 2005, 272, 538-549.
37. Lopatin, S.A.; Derbeneva, M.S.; Kulikov, S.N.; Varlamov, V.P.; Shpigun, O.A. Fractionation of chitosan by ultrafiltration. J. Anal. Chem. 2009, 64, 648-651.
38. Haebel, S.; Bahrke, S.; Peter, M.G. Quantitative sequencing of complex mixtures of heterochitooligosaccharides by MALDI-linear ion trap mass spectrometry. Anal. Chem. 2007, 79, 5557-5566.
39. Le Dévédec, F.; Bazinet, L.; Furtos, A.; Venne, K.; Brunet, S.; Mateescu, M.A. Separation of chitosan oligomers by immobilized metal affinity chromatography. J. Chromatogr. A 2008, 1194, 165-171.
40. Pichyangkura, R.; Kudan, S.; Kuttiyawong, K.; Sukwattanasinitt, M.; Aiba, S. Quantitative production of 2-acetamido-2-deoxy-D-glucose from crystalline chitin by bacterial chitinase. Carbohydr. Res. 2002, 337, 557-559.
41. Sashiwa, H.; Fujishima, S.; Yamano, N.; Kawasaki, N.; Nakayama, A.; Muraki, E.; Sukwattanasinitt, M.; Pichyangkurac, R.; Aiba, S. Enzymatic production of N-acetyl-D-glucosamine from chitin. Degradation study of N-acetylchitooligosaccharide and the effect of mixing of crude enzymes. Carbohydr. Polym. 2003, 51, 391-395.
42. Il'ina, A.V.; Zueva, O.Y.; Lopatin, S.A.; Varlamov, V.P. Enzymatic hydrolysis of α-chitin. Appl. Biochem. Microbiol. 2004, 40, 35-38.
43. Sukwattanasinitt, M.; Zhu, H.; Sashiwa, H.; Aiba, S. Utilization of commercial non-chitinase enzymes from fungi for preparation of 2-acetamido-2-deox-D-glucose from β-chitin. Carbohydr. Res. 2002, 337, 133-137.
44. Sashiwa, H.; Fujishima, S.; Yamano, N.; Kawasaki, N.; Nakayama, A.; Muraki, E.; Hiraga, K.; Oda, K.; Aiba, S. Production of N-acetyl-D-glucosamine from α-chitin by crude enzymes from Aeromonas hydrophila H-2330. Carbohydr. Res. 2002, 337, 761-763.
45. Thamthiankul, S.; Suan-Ngay, S.; Tantimavanich, S.; Panbangred, W. Chitinase from Bacillus thuringiensis subsp pakistani. Appl. Microbiol. Biotechnol. 2001, 56, 395-401.
46. Katta, S.; Ankati, S.; Podile, A.R. Chitooligosaccharides are converted to N-acetylglucosamine by N-acetyl-β-hexosaminidase from Stenotrophomonas maltophilia. FEMS Microbiol. Lett. 2013, 348, 19-25.
47. Lan, X.; Ozawa, N.; Nishiwaki, N.; Kodaira, R.; Okazaki, M.; Shimosaka, M. Purification, cloning, and sequence analysis of β-N-acetylglucosaminidase from the chitinolytic bacterium Aeromonas hydrophila strain SUWA-9. Biosci. Biotechnol. Biochem. 2004, 68, 1082-1090.
48. Kuk, J.H.; Jung, W.J.; Jo, G.H.; Ahn, J.S.; Kim, K.Y.; Park, R.D. Selective preparation of N-acetyl-D-glucosamine and N, iV'-diacetylchitobiose from chitin using a crude enzyme preparation from Aeromonas sp. Biotechnol. Lett. 2005, 27, 7-11.
49. Kuk, J.H.; Jung, W.J.; Jo, G.H.; Kim, Y.C.; Kim, K.Y.; Park, R.D. Production of N-acetyl-β-D-glucosamine from chitin by Aeromonas sp. GJ-18 crude enzyme. Appl. Microbiol. Biotechnol. 2005, 68, 384-389.
50. Kuk, J.H.; Jung, W.J.; Jo, G.H.; Kim, K.Y.; Park, R.D. Production of N, N′-diacetylchitobiose from chitin using temperature-sensitive chitinolytic enzyme preparations of Aeromonas sp. GJ-18. World J. Microbiol. Biotechnol. 2006, 22, 135-139.
51. Martinez, E.A.; Boer, H.; Koivula, A.; Samain, E.; Driguez, H.; Armand, S.; Cottaz, S. Engineering chitinases for the synthesis of chitin oligosaccharides: Catalytic amino acid mutations convert the GH-18 family glycoside hydrolases into transglycosylases. J. Mol. Catalys. B Enzym. 2012, 74, 89-96.
52. Tanaka, T.; Fukui, T.; Atomi, H.; Imanaka, T. Characterization of an exo-β-D-glucosaminidase involved in a novel chitinolytic pathway from the hyperthermophilic archaeon Thermococcus kodakaraensis KOD1. J. Bact. 2003, 185, 5175-5181.
53. Yamasaki, Y.; Hayashi, I.; Ohta, Y.; Nakagawa, T.; Kawamukai, M.; Matsuda, H. Purification and mode of action of chitosanolytic enzyme from Enterobacter sp. G-1. Biosci. Biotechnol. Biochem. 1993, 57, 444-449.
54. Makino, A.; Sakamoto, J.; Ohmae, M.; Kobayashi, S. Effect of fluorine substituent on the chitinase-catalyzed polymerization of sugar oxazoline derivatives. Chem. Lett. 2006, 35, 160-161.
55. Makino, A.; Ohmae, M.; Kobayashi, S. Chitinase-catalyzed copolymerization to a chitin derivative having glucosamine unit in controlled proportion. Polym. J. 2006, 38, 1182-1188.
56. Takiguchi, Y.; Shimahara, K. N, N-Diacetylchitobiose production from chitin by Vibrio anguillarum strain E-383a. Lett. Appl. Microbiol. 1988, 6, 129-131.
57. Ilankovan, P.; Hein, S.; Ng, C.H.; Trung, T.S.; Stevens, W.F. Production of N-acetyl chitobiose from various chitin substrates using commercial enzymes. Carbohydr. Polym. 2006, 63, 245-250.
58. Wang, S.L.; Liu, C.P.; Liang, T.W. Fermented and enzymatic production of chitin/chitosan oligosaccharides by extracellular chitinases from Bacillus cereus TKU027. Carbohydr. Polym. 2012, 90, 1305-1313.
59. Wang, C.Y.; Hsieh, Y.Z. Analysis of chitin oligosaccharides by capillary electrophoresis with laser-inducedfluorescence. J. Chromatogr. A 2002, 979, 431-438.
60. Saito, J.; Kita, A.; Higuchi, Y.; Nagata, Y.; Ando, A.; Miki, K. Crystal structure of chitosanase from Bacillus circulans MH-K1 at 1.6-angstrom resolution and its substrate recognition mechanism. J. Biol. Chem. 1999, 274, 30818-30825.
61. Fukamizo, T.; Ohkawa, T.; Ikeda, Y.; Goto, S. Specificity of chitosanase from Bacillus pumilus. Biochim. Biophys. Acta 1994, 1205, 183-188.
62. Cheng, C.Y.; Chang, C.H.; Wu, Y.J.; Li, Y.K. Exploration of glycosyl hydrolase family 75, a chitosanase from Aspergillus fumigatus. J. Biol. Chem. 2006, 281, 3137-3144.
63. Fukamizo, T.; Brzezinski, R. Chitosanase from Streptomyces sp. strain N174: A comparative review of its structure and function. Biochem. Cell Biol. 1997, 75, 687-696.
64. Choi, Y.J.; Kim, E.J.; Piao, Z.; Yun, Y.C.; Shin, Y.C. Purification and characterization of chitosanase from Bacillus sp. strain KCTC 0377BP and its application for the production of chitosan oligosaccharides. Appl. Environ. Microbiol. 2004, 70, 4522-4531.
65. Kurakake, M.; You, S.; Nakagawa, K.; Sugihara, M.; Komaki, T. Properties of chitosanase from Bacillus cereus S1. Curr. Microbiol. 2000, 40, 6-9.
66. Park, R.D.; Rhee, C.O.; Lee, H.C.; Cho, C.S.; Jo, D.H. A comparative study of chitooligosaccharide production from chitosan. J. Chitin Chitosan 1999, 4, 96-101.
67. Yoon, H.G.; Ha, S.C.; Lim, Y.H.; Cho, H.Y. New thermostable chitosanase from Bacillus sp.: Purification and characterization. J. Microbiol. Biotechnol. 1998, 8, 449-454.
68. Lee, H.W.; Choi, J.W.; Han, D.P.; Park, M.J.; Lee, N.W.; Yi, D.H. Purification and characteristics of chitosanase from Bacillus sp. HW-002. J. Microbiol. Biotechnol. 1996, 6, 19-25.
69. Jeon, Y.J.; Kim, S.K. Production of chitooligosaccharides using ultrafilteration membrane reactor and their antibacterial activity. Carbohydr. Polym. 2000, 41, 133-144.
70. Pelletier, A.; Sygusch, J. Purification and characterization of three chitosanase activities from Bacillus megaterium P1. Appl. Environ. Microbiol. 1990, 56, 844-848.
71. Shimosaka, M.; Nogawa, M.; Wang, X.Y.; Kumehara, M.; Okazaki, M. Production of two chitosanases from a chitosan-assimilating bacterium, Acinetobacter sp. strain CHB101. Appl. Environ. Microbiol. 1995, 61, 438-442.
72. Wang, S.L.; Tseng, W.N.; Liang, T.W. Biodegradation of shellfish wastes and production of chitosanases by a squid pen-assimilating bacterium, Acinetobacter calcoaceticus TKU024. Biodegradation 2011, 22, 939-948.
73. Nanjo, F.; Katsumi, R.; Sakai, K. Purification and characterization of an exo-β-D-glucosaminidase, a novel type of enzyme, from Nocardia orientalis. J. Biol. Chem. 1990, 265, 10088-10094.
74. Park, J.K.; Shimono, K.; Ochiai, N.; Shigeru, K.; Kurita, M.; Ohta, Y.; Tanaka, K.; Matsuda, H.; Kawamukai, M. Purification, characterization, and gene analysis of a chitosanase (ChoA) from Matsuebacter chitosanotabidus 3001. J. Bact. 1999, 181, 6642-6649.
75. Kim, S.Y.; Shon, D.H.; Lee, K.H. Purification and characteristics of two types of chitosanases from Aspergillus fumigatus. J. Microbiol. Biotechnol. 1998, 8, 568-574.
76. Jung, W.J.; Kuk, J.H.; Kim, K.Y.; Jung, K.C.; Park, R.D. Purification and characterization of exo-β-D-glucosaminidase from Aspergillus fumigatus S-26. Protein Expr. Purif. 2006, 45, 125-131.
77. Zhang, X.Y.; Dae, A.L.; Zhang, X.K.; Kuroiwa, K. Purification and characterization of chitosanase and exo-β-D-glucosaminidase from Koji Mold, Aspergillus oryzae IAM2660. Biosci. Biotechnol. Biochem. 2000, 64, 1896-1902.
78. Nogawa, M.; Takahashi, H.; Kasiwagi, A.; Ohshima, K.; Okada, H.; Morikawa, Y. Purification and characterization of exo-β-D-glucosaminidase from a cellulolytic fungus, Trichoderma reesei PC-3-7. Appl. Envoron. Microbiol. 1998, 64, 890-895.
79. Lin, H.; Wang, H.; Xue, C.; Ye, M. Preparation of chitosan oligomers by immobilized papain. Enzyme Microb. Technol. 2002, 31, 588-592.
80. Lee, D.X.; Xia, W.S.; Zhang, J.L. Enzymatic preparation of chitooligosaccharides by commercial lipase. Food Chem. 2008, 111, 291-295.
81. Zhang, H.; Du, Y.; Yu, X.; Mitsutomi, M.; Aiba, S. Preparation of chitooligosaccharides from chitosan by acomplex enzyme. Carbohydr. Res. 1999, 320, 257-260.
82. Mahata, M.; Shinya, S.; Masaki, E.; Yamamoto, T.; Ohnuma, T.; Brzezinski, R.; Mazumder, T.K.; Yamashita, K.; Narihiro, K.; Fukamizo, T. Production of chitooligosaccharides from Rhizopus oligosporus NRRL2710 cells by chitosanase digestion. Carbohydr. Res. 2014, 383, 27-33.
83. Yalpani, M.; Pantaleone, D. An examination of the unusual susceptibility of aminoglycans to enzymatic hydrolysis. Carbohydr. Res. 1994, 256, 159-175.
84. Nguyen, A.D.; Huang, C.C.; Liang, T.W.; Nguyen, V.B.; Pan, P.S.; Wang, S.L. Production and purification of a fungal chitosanase and chitooligomers from Penicillium janthinellum D4 and discovery of the enzyme activators. Carbohydr. Polym. 2014, 108, 331-337.
85. Gao, X.A.; Jung, W.J.; Kuk, J.H.; Park, R.D. Reaction pattern of Bacillus cereus D-11 chitosanase on chito-oligosaccharide alcohols. J. Microbiol. Biotechnol. 2009, 19, 358-361.
86. Pantaleone, D.; Yalpani, M.; Scollar, M. Unusual susceptibility of chitosan to enzymic hydrolysis. Carbohydr. Res.1992, 237, 325-332.
87. Aiba, S.I. Preparation of N-acetylchitooligosaccharides from lysozymatic hydroxylate of partially N-acetylated chitosans. Carbohydr. Res. 1994, 261, 297-306.
88. Kumar, A.B.V.; Gowda, L.R.; Tharanathan, R.N. Non-specific depolymerization of chitosan by pronase and characterization of the resultant products. Eur. J. Biochem. 2004, 271, 713-723.
89. Xie, Y.;Hu, J.; Wei, Y.; Hong, X. Preparation of chitooligosaccharides by the enzymatic hydrolysis of chitosan. Polym. Degrad. Stab. 2009, 94, 1895-1899.
90. Wu, S. Preparation of chitooligosaccharides from Clanis bilineata larvae skin and their antibacterial activity. Int. J. Biol. Macromol. 2012, 51, 1147-1150.
91. Zhao, Y.; Park, R.D.; Muzzarelli, R.A.A. Chitin deacetylases: Properties and applications. Mar. Drugs 2010, 8, 24-46.
92. Zhao, Y.; Kim, Y.J.; Oh, K.T.; Nguyen, V.N.; Park, R.D. Production and characterization of extracellular chitin deacetylase from Absidia corymbifera DY-9. J. Korean Soc. Appl. Biol. Chem. 2010, 53, 119-126.
93. Zhao, Y.; Ju, W.T.; Jo, G.H.; Jung, W.J.; Park, R.D. Perspectives of chitin deacetylase research. In Biotechnology of Biopolymers; Elnashar, M., Ed.; InTech: Rijeka, Croatia, 2011; pp. 131-144.
94. Kim, Y.J.; Zhao, Y.; Oh, K.T.; Nguyen, V.N.; Park, R.D. Enzymatic deacetylation of chitin by extracellular chitin deacetylase from newly screened Mortierella sp. DY-52. J. Microbiol. Biotechnol. 2008, 18, 759-766.
95. Tanaka, T.; Fukui, T.; Fujiwara, S.; Atomi, H.; Imanaka, T. Concerted action of diacetylchitobiose deacetylase and exo-beta-D-glucosaminidase in a novel Biotechnology of Biopolymers chitinolytic pathway in the hyperthermophilic archaeon Thermococcus kodakaraensis KOD1. J. Biol. Chem. 2004, 279, 30021-30027.
96. Tokuyasu, K.; Ono, H.; Ohnishi-Kameyama, M.; Hayashi, K.; Mori, Y. Deacetylation of chitin oligosaccharides of dp 2-4 by chitin deacetylase from Colletotrichum lindemuthianum. Carbohydr. Res. 1997, 303, 353-358.
97. Alfonso, C.; Nuero, O.M.; Santamarla, F.; Reyes, F. Purification of a heat-stable chitin deacetylase from Aspergillus nidulans and its role in cell wall degradation. Curr. Microbiol.1995, 30, 49-54.
98. Aguila, E.M.D.; Gomes, L.P.; Andrade, CT.; Silva, J.T.; Paschoalin, V.M.F. Biocatalytic production of chitosan polymers from shrimp shells, using a recombinant enzyme produced by Pichia pastoris. Am. J. Mol. Biol. 2012, 2, 341-350.
99. Blair, D.E.; Hekmat, O.; Schuttelkopf, A.W.; Shrestha, B.; Tokuyasu, K.; Withers, S.G.; van Aalten, D.M. Structure and mechanism of chitin deacetylase from the fungal pathogen Colletotrichum lindemuthianum. Biochemistry 2006, 45, 9416-9426.
100. Martinou, A.; Bouriotis, V.; Stokke, B.T.; Vårum, K.M. Mode of action of chitin deacetylase from Mucor rouxii on partially N-acetylated chitosans. Carbohydr. Res. 1998, 311, 71-78.
101. Hattori, T.; Sakabe, Y.; Ogata, M.; Michishita, K.; Dohra, H.; Kawagishi, H.; Totani, K.; Nikaido, M.; Nakamura, T.; Koshino, H.; Usui, T. Enzymatic synthesis of an a-chitin-like substance via lysozyme-mediated transglycosylation. Carbohydr. Res. 2012, 347, 16-22.
102. Shimoda, K.; Nakajima, K.; Hiratsuka, Y.; Nishimura, S.I.; Kurita, K. Efficient preparation of β-(l→-6)-(GlcNAc)2 by enzymatic conversion of chitin and chito-oligosaccharides. Carbohydr. Polym.1996, 29, 149-154.
103. Matsumura, S.; Yao, E.; Toshima, K. One-step preparation of alkyl β-D-glucosaminide by the transglycosylation of chitosan and alcohol using purified exo-β-D-glucosaminidase. Biotechnol. Lett. 1999, 21, 451-456.
104. Usui, T.; Matsu, H.; Isobe, K. Enzymic synthesis of useful chito-oligosaccharides utilizing transglycosylation by chitinolytic enzymes in a buffer containing ammonium sulfate. Carbohydr. Res. 1990, 203, 65-77.
105. Akiyama, K.; Kawazu, K.; Kobayashi, A. A novel method for chemo-enzymatic synthesis of elicitor-active chitosan oligomers and partially N-acetylated chitin oligomers using N-acetylated chitotriose as substrates in a lysozyme-catalyzed transglycosylation reaction system. Carbohydr. Res. 1995, 279, 151-160.
106. Fujimoto, Y.; Hattori, T.; Uno, S.; Murata, T.; Usui, T. Enzymatic synthesis of gentiooligosaccharides by transglycosylation with β-glycosidases from Penicillium multicolor. Carbohydr. Res. 2009, 344, 972-978.
107. Kobayashi, S.; Makino, A.; Matsumoto, H.; Kunii, S.; Ohmae, M.; Kiyosada, T.; Makiguchi, K.; Matsumoto, A.; Horie, M.; Shoda, S.I. Enzymatic polymerization to novel polysaccharides having a glucose-N-acetylglucosamine repeating unit, a cellulose-chitin hybrid polysaccharide. Biomacromolecules 2006, 7, 1644-1656.
108. Kobayashi, S.; Makino, A. Enzymatic polymer synthesis: An opportunity for green polymer chemistry. Chem. Rev. 2009, 109, 5288-5353
109. Kadokawa, J.I. Precision polysaccharide synthesis catalyzed by enzymes. Chem. Rev. 2011, 111, 4308-4345.
110. Shoda, S.; Izumi, R.; Fujita, M. Green process in glycotechnology. Bull. Chem. Soc. Jpn. 2003, 76, 1-13.
111. Kadokawa, J.; Shoda, S.J. New methods for architectures of glyco-materials. Synthetic Org. Chem. Jpn. 2003, 61, 1207.
112. Misawa, Y.; Lohavisavapanichi, C; Shoda, S. Chemo-enzymatic synthesis of oligosaccharides having a polymerizable group at the reducing end. Glycoconj. J. 1999, 16, S122.
113. Shoda, S.; Fujita, M.; Lohavisavapanichi, C; Misawa, Y.; Ushizaki, K.; Tawata, Y.; Kuriyama, M.; Kohri, M.; Kuwata, H.; Watanabe, T. Efficient method for the elongation of the N-acetylglucosamine unit by combined use of chitinase and β-galactosidase. Helv. Chim. Acta 2002, 85, 3919.
114. Kadokawa, J.; Shoda, S. Enzymatic synthesis of glyco-macromonomers. Sen'i Gakkaishi 2003, 59, 74-78.
115. Shoda, S.; Misawa, Y.; Nishijima, Y.; Tawata, Y.; Kotake, T.; Noguchi, M.; Kobayashi, A.; Watanabe, T. Chemo-enzymatic synthesis of novel oligo-N-acetyllactosamine derivatives having a β(1-4)-β(1-6) repeating unit by using transition state analogue substrate. Cellulose 2006, 13, 477-484.
116. Watanabe, T.; Kobori, K.; Miyashita, K.; Fujii, T.; Sakai, H.;Uchida, M.; Tanaka, H. Identification of glutamic acid 204 and aspartic acid 200 in chitinase A1 of Bacillus circulans WL-12 as essential residues for chitinase activity. J. Biol. Chem. 1993, 268, 18567-18572.
117. Watanabe, T.; Suzuki, K.; Oyanagi, W.; Ohnishi, K.; Tanaka, H. Gene cloning of chitinase A1 from Bacillus circulans WL-12 revealed its evolutionary relationship to Serratia chitinase and to the type III homology units of fibronectin. J. Biol. Chem. 1990, 265, 15659-15665.
118. Sakamoto, J.; Watanabe, T.; Ariga, Y.; Kobayashi, S. Ring-opening glycosylation of a chitobiose oxazoline catalyzed by a non-chitinolytic mutant of chitinase. Chem. Lett. 2001, 30, 1180-1181.
119. Ochiai, H.; Ohmae, M.; Kobayashi, S. Enzymatic synthesis of alternatingly 6-O-carboxymethylated chitotetraose by selective glycosidation with chitinase catalysis. Chem. Lett. 2004, 33, 694-695.
120. Ochiai, H.; Ohmae, M.; Kobayashi, S. Enzymatic glycosidation of sugar oxazolines having a carboxylate group catalyzed by chitinase. Carbohydr. Res. 2004, 339, 2769-2788.
121. Makino, A.; Kurosaki, K.; Ohmae, M.; Kobayashi, S. Chitinase-catalyzed synthesis of alternatingly N-Deacetylated chitin: A chitin-chitosan hybrid polysaccharide. Biomacromolecules 2006, 7, 950-957.
122. Villa-Lerma, G.; Gonzalez-Marquez, H.; Gimeno, M.; Lopez-Luna, A.; Barzana, E.; Shirai, K. Ultrasonication and steam-explosion as chitin pretreatments for chitin oligosaccharide production by chitinases of Lecanicillium lecanii. Biores. Technol. 2013, 146, 794-798.
123. Nakagawa, Y.S.; Oyama, Y.; Kon, N.; Nikaido, M.; Tanno, K.; Kogawa, J.; Inomata, S.; Masui, A.; Yamamura, A.; Kawaguchi, M.; et al. Development of innovative technologies to decrease the environmental burdens associated with using chitin as a biomass resource: Mechanochemical grinding and enzymatic degradation. Carbohydr. Polym. 2011, 83, 1843-1849.
124. Sato, T.; Asada, K.; Takeda, M.; Tanno, K. Mechano-chemical synthesis of compound powders in ZnO-TiO2 system by a new high intensive ball mill. J. Jpn. Soc. Powder Metall. 2006, 53, 62-67.
125. Takeda, T.; Nikaido, M.; Totani, T.; Obara, M.; Nakano, Y.; Uchimiya, H. Evaluation of high intensive ball mill method for effective saccharification of plant cell wall materials. J. Appl. Glycosci. 2009, 56, 71-76.
126. Wu, Q.; Miao, Y. Mechanochemical effects of micronization on enzymatic hydrolysis of corn flour. Carbohydr. Polym. 2008, 72, 398-402.
127. Fujimoto, S.; Inoue, H.; Yano, S.; Sakaki, T.; Minowa, T.; Endo, T. Bioethanol production from lignocellulosic biomass requiring no sulfuric acid: Mechanochemical pretreatment and enzymic saccharification. J. Jpn. Petrol. Inst. 2008, 51, 264-273.
128. Van Craeyveld, V.; Delcour, J.A.; Courtin, C.M. Ball milling improves extractability and affects molecular properties of Psyllium (Plantago ovate Forsk) seed husk arabinoxylan. J. Agric. Food Chem. 2008, 56, 11306-11311.
129. Reese, E.T.; Siu, R.G.H.; Levinson, H.S. The biological degradation of soluble cellulose derivatives and its relationship to the mechanism of cellulose hydrolysis. J. Bacteriol. 1950, 59, 485-497.
130. Vaaje-Kolstad, G.; Westereng, B.; Horn, S.J.; Liu, Z.; Zhai, H.; Sørlie, M.; Eijsink, V.G.H. An oxidative enzyme boosting the enzymatic conversion of recalcitrant polysaccharides. Science 2010, 330, 219-222.
131. Shinohara, M.L.; Ihara, M.; Abo, M.; Hashida, M.; Takagi, S.; Beck, T.C. A novel thermostable branching enzyme from an extremely thermophilic bacterial species, Rhodothermus obamensis. Appl. Microbiol. Biotechnol. 2001, 57, 653-659.
132. Montilla, A.; Ruiz-Matute, A.I.; Corzo, N.; Cecilia Giacomini, C.; Irazoqui, G. Enzymatic generation of chitooligosaccharides from chitosan using soluble and immobilized glycosyltransferase (Branchzyme). J. Agric. Food Chem. 2013, 61, 10360-10367.
133. Heggset, E.B.; Dybvik, A.I.; Hoell, I.A.; Norberg, A.L.; Sørlie, M.; Eijsink, V.G.H.; Vårum, K.M. Degradation of chitosans with a family 46 chitosanase from Streptomyces coelicolor A3(2). Biomacromolecules 2010, 11, 2487-2497.
134. Horn, S.J.; Sørbotten, A.; Synstad, B.; Sikorski, P.; Sørlie, M.; Vårum, K.M.; Eijsink, V.G. Endo/exo mechanism and processivity of family 18 chitinases produced by Serratia marcescens. FEBS J. 2006, 273, 491-503.
135. Fukamizo, T.; Honda, Y.; Goto, S.; Boucher, I.; Brzezinski, R. Reaction mechanism of chitosanase from Streptomyces sp. N174. Biochem. J. 1995, 311, 377-383.
136. Amano, K.; Ito, E. The action of lysozyme on partially deacetylated chitin. Eur. J. Biochem. 1978, 85, 97-104.
137. Sikorski, P.; Stokke, B.T.; Sørbotten, A.; Vårum, K.M.; Horn, S.J.; Eijsink, V.G. Development and application of a model for chitosan hydrolysis by a family 18 chitinase. Biopolymers 2005, 77, 273-285.
138. Heggset, E.B.; Hoell, I.A.; Kristoffersen, M.; Eijsink, V.G.; Vårum, K.M. Degradation of chitosans with chitinase G from Streptomyces coelicolor A3(2): Production of chito-oligosaccharides and insight into subsite specificities. Biomacromolecules 2009, 10, 892-899.
139. Mitsutomi, M.; Hata, T.; Kuwahara, T. Purification and characterization of novel chitinases from Streptomyces griseus Hut 6037. J. Ferment. Bioeng. 1995, 80, 153-158.
140. Sasaki, C.; Vårum, K.M.; Itoh, Y.; Tamoi, M.; Fukamizo, T. Rice chitinases: Sugar recognition specificities of the individual subsites. Glycobiology 2006, 16, 1242-1250.
141. Horn, S.J.; Sikorski, P.; Cederkvist, J.B.; Vaaje-Kolstad, G.; Sørlie, M.; Synstad, B.; Vriend, G.; Vårum, K.M.; Eijsink, V.G.H. Costs and benefits of processivity in enzymatic degradation of recalcitrant polysaccharides. Proc. Natl. Acad. Sci. USA 2006, 103, 18089-18094.
142. Sikorski, P.; Sørbotten, A.; Horn, S.J.; Eijsink, V.G.; Vårum, K.M. Serratia marcescens chitinases with tunnel-shaped substrate-binding grooves show endo activity and different degrees of processivity during enzymatic hydrolysis of chitosan. Biochemistry 2006, 45, 9566-9574.
143. Gyore, J.; Parameswar, A.R.; Hebbard, C.F.F.; Oh, Y.; Bi, E.; Demchenko, A.V.; Price, N.P.; Orlean, P. 2-Acylamido analogues of N-acetylglucosamine prime formation of chitin oligosaccharides by yeast chitin synthase 2. J. Biol. Chem. 2014, 289, 12835-12841.
144. Liang, T.W.; Hsieh, J.L.; Wang, S.L. Production and purification of a protease, a chitosanase, and chitin oligosaccharides by Bacillus cereus TKU022 fermentation. Carbohydr. Res. 2012, 362, 38-46.
145. Vandanarachchi, J.K.; Kurukulasuriya, M.S.; Kim, S.K. Chitin, chitosan, and their oligosaccharides in food industry. In Chitin, Chitosan, Oligosaccharides and Their Derivatives; Kim, S.K., Ed.; CRC Press: Boca Raton, FL, USA, 2011; pp. 543-560.
146. Jeon, Y.J.; Kim, S.K. Continuous production of chitooligosaccharides using a dual reactor system. Process Biochem. 2000, 35, 623-632.