Synthesis of fluorinated chitin derivatives via enzymatic polymerization

Macromolecular Bioscience

Volumn 6, Issue 10, 2006, Pages 862-872

  Makino, Akira ^a   Ohmae, Masashi ^a   Kobayashi, Shiro ^a,b  

^a KYOTO UNIVERSITY   (Japan)

^b KYOTO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Chitinase; Enzymatic polymerization; Fluorinated chitin derivatives; Transition state analogue substrate monomer

Indexed keywords

CRYSTAL STRUCTURE; CRYSTALLINE MATERIALS; DERIVATIVES; ENZYME KINETICS; MONOMERS; RING OPENING POLYMERIZATION;

CHITINASE; ENZYMATIC POLYMERIZATION; FLUORINATED CHITIN DERIVATIVES; TRANSITION STATE ANALOGUE SUBSTRATE MONOMERS;

CHITIN;

6 FLUOROCHITOBIOSE OXAZOLINE DERIVATIVE; 6' FLUOROCHITOBIOSE OXAZOLINE DERIVATIVE; 6,6' DIFLUOROCHITOBIOSE OXAZOLINE DERIVATIVE; CHITIN DERIVATIVE; CHITINASE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL STRUCTURE; FLUORINATION; PROTEIN POLYMERIZATION; SYNTHESIS;

CATALYSIS; CHITIN; CHITINASE; DRUG DESIGN; FLUORINE COMPOUNDS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR CONFORMATION; POLYMERS; STRUCTURE-ACTIVITY RELATIONSHIP;

BACILLUS SP.;

EID: 33751538594     PISSN: 16165187     EISSN: 16165195     Source Type: Journal    
DOI: 10.1002/mabi.200600128     Document Type: Article

References (40)

1. K. Kobayashi, T. Kondo, Macromolecules 1997, 30, 6531.
2. [2a] N. Kasuya, K. Iiyama, A. Ishizu, Carbohydr. Res. 1992, 229, 131;
3. [2b] N. Kasuya, K. Iiyama, G. Meshitsuka, A. Ishizu, Carbohydr. Res. 1994, 260, 251;
4. [2c] J. E. Sealey, C. E. Frazier, G. Samaranayake, W. G. Glasser, J. Polym. Sci., Polym. Phys. Ed. 2000, 38, 486;
5. [2d] C. E. Frazier, W. G. Glasser, J. Appl. Polym. Sci. 1995, 58, 1063.
6. B. E. Smart, "Characteristics of C-F Systems", in: Organofluorine Chemistry: Principles and Commercial Applications, R. E. Banks, B. E. Smart, J. C. Tatlow, Eds., Plenum, New York 1994, p. 57.
7. [4a] I. Ojima, J. R. McCarthy, J. T. Welch, "Biomedical Frontiers of Fluorine Chemistry", ACS Symp. Ser., ACS, Washington, DC 1996, p. 639;
8. [4b] R. Filler, "Organic Chemistry in Medical Chemistry and Biomedical Applications", Elsevier, Amsterdam 1993;
9. [4c] J. T. Welch, S. Eswaraksrishnan, "Fluorine in Bioorganic Chemistry", Wiley, New York 1991;
10. [4d] R. Filler, K. Kirk, "Biological Properties of Fluorinated Compounds", in: Chemistry of Organic Fluorine Compounds II: A Critical Review, ACS Monograph 187, M. Hudlicky, A. Pavlath, Eds., ACS, Washington, DC 1995, p. 1011;
11. [4e] A. J. Elliot, "Fluorinated Pharmaceuticals", in: Chemistry of Organic Fluorine Compounds II: A Critical Review, ACS Monograph 187, M. Hudlicky, A. E. Pavlath, Eds., ACS, Washington, DC 1995, p. 1119.
12. [5a] D. Carwright, "Recent Developments in Fluorine-Containing Agrochemicals", in: Organofluorine Chemistry: Principles and Commercial Applications, R. E. Banks, B. E. Smart, J. C. Tatlow, Eds., Plenum, New York 1994, p. 237;
13. [5b] R. W. Lang, "Fluorinated Agrochemicals", in: Chemistry of Organic Fluorine Compounds II, ACS Monograph 187, M. Hudlicky, A. E. Pavlath, Eds., ACS, Washington, DC 1995, p. 1143.
14. S. Salmon, S. M. Hudson, J. Macromol. Sci., Rev. Macromol. Chem. Phys. 1997, C37, 199.
15. [7a] R. A. A. Muzzarelli, "Chitin", Pergamon, Oxford 1977;
16. [7b] M. N. V. R. Kumar, R. A. A. Muzzarelli, C. Muzzarelli, H. Sashiwa, A. J. Domb, Chem. Rev. 2004, 104, 6017.
17. N. L. B. M. Yusof, A. Wee, L. Y. Lim, E. Khor, J. Biomed. Mater. Res. 2003, 66A, 224.
18. S.-I. Nishimura, H. Kai, K. Shinada, T. Yoshida, S. Tokura, K. Kurita, H. Nakashima, N. Yamamoto, T. Uryu, Carbohydr. Res. 1998, 306, 427.
19. N. Sakairi, A. Shirai, S. Miyazaki, H. Tashiro, Y. Tsuji, H. Kawahara, T. Yoshida, N. Nishi, S. Tokura, Kobunshi Ronhunshu 1998, 55, 212.
20. S.-I. Nishimura, N. Nishi, S. Tokura, K. Nishimura, I. Azuma, Carbohydr. Res. 1986, 146, 251.
21. K. S. Chow, E. Khor, Carbohydr. Polym. 2002, 47, 357.
22. [13a] S. Kobayashi, H. Uyama, S. Kimura, Chem. Rev. 2001, 101, 3793;
23. [13b] S. Kobayashi, H. Uyama, M. Ohmae, Bull. Chem. Soc. Jpn. 2001, 74, 613;
24. [13c] S. Kobayashi, J. Sakamoto, S. Kimura, Prog. Polym. Sci. 2001, 26, 1525;
25. [13d] S. Kobayashi, J. Polym. Sci., Polym. Chem. Ed. 1999, 37, 3041;
26. [13e] S. Kobayashi, S.-I. Shoda, H. Uyama, "Catalysis in Precision Polymerization", S. Kobayashi, Ed., John Wiley & Sons, Chichester 1997, Chapter 8;
27. [13f] S. Kobayashi, S.-I. Shoda, H. Uyama, Adv. Polvm. Sci. 1995, 121, 1.
28. S. Kobayashi, T. Kiyosada, S.-I. Shoda, J. Am. Chem. Soc. 1996, 118, 13113.
29. J. Sakamoto, J. Sugiyama, S. Kimura, T. Imai, T. Itoh, T. Watanabe, S. Kobayashi, Macromolecules 2000, 33, 4155.
30. A. Makino, K. Kurosaki, M. Ohmae, S. Kobayashi, Biomacromolecules 2006, 7, 950.
31. S. Kobayashi, A. Makino, H. Matsumoto, S. Kunii, M. Ohmae, T. Kiyosada, K. Makiguchi, A. Matsumoto, M. Horie, S.-I. Shoda, Biomacromolecules 2006, 7, 1644.
32. [18a] B. Henrissat, Biochem. J. 1991, 280, 309;
33. [18b] B. Henrissat, A. Bairoch, Biochem. J. 1993, 293, 781;
34. [18c] B. Henrissat, A. Bairoch, Biochem. J. 1996, 316, 695;
35. [18d] G. Davies, B. Henrissat, Structure 1995, 3, 853;
36. [18e] B. Henrissat, G. Davies, Curr. Opin. Struct. Biol. 1997, 7, 637.
37. K. Kurita, K. Sugita, N. Kodaira, M. Hirakawa, J. Yang, Biomacromolecules 2005, 6, 1414.
38. A. Makino, J. Sakamoto, M. Ohmae, S. Kobayashi, Chem. Lett. 2006, 35, 160.
39. [21a] The optimal hydrolysis condition of chitinase was provided from the supplier as pH 7.8-8.6;
40. [21b] C. Wiwat, P. Siwayaprahm, A. Bhumiratana, Curr. Microbiol. 1999, 39, 134.