Enzymatic synthesis of 3-O-methylated chitin oligomers from new derivatives of a chitobiose oxazoline

Chemistry Letters

Volumn 33, Issue 6, 2004, Pages 698-699

  Sakamoto, Junji ^a   Kobayashi, Shiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CHITIN DERIVATIVE; OLIGOMER; OXAZOLINE DERIVATIVE;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; ENZYME MECHANISM; OLIGOMERIZATION; TECHNIQUE;

EID: 4444329418     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2004.698     Document Type: Article

References (17)

1. R. Minke and J. Blackwell, J. Mol. Biol., 120, 167 (1978).
2. K. Kurita, Prog. Polym. Sci, 26, 1921 (2001).
3. K. Tsukada, T. Matsumoto, K. Aizawa, A. Tokoro, R. Naruse, S. Suzuki, and M. Suzuki, Jpn. J. Cancer Res., 81, 259 (1990).
4. E. Okamoto, T. Kiyosada, S. Shoda, and S. Kobayashi, Cellulose, 4, 161 (1997).
5. D. M. Chipman and N. Sharon, Science, 165, 454 (1969).
6. a) S. Kobayashi, S. Shoda, and H. Uyama, in "Catalysis in Precision Polymerization," ed. by S. Kobayashi, John Wiley & Sons, Chichester (1997), Chap. 8.
7. b) S. Kobayashi, H. Uyama, and M. Ohmae, Bull. Chem. Soc. Jpn., 74, 613 (2001).
8. c) S. Kobayashi, J. Sakamoto, and S. Kimura, Prog. Polym. Sci., 26, 1525 (2001).
9. d) S. Kobayashi, H. Uyama, and S. Kimura, Chem. Rev., 101, 3793 (2001).
10. a) T. Kiyosada, E. Takada, S. Shoda, and S. Kobayashi, Polym. Prepr. Jpn., 44, 660 (1995).
11. b) S. Kobayashi, T. Kiyosada, and S. Shoda, J. Am. Chem. Soc., 118, 13113 (1996).
12. c) S. Kobayashi, T. Kiyosada, and S. Shoda, Tetrahedron Lett., 38, 2111 (1997).
13. d) J. Sakamoto, J. Sugiyama, S. Kimura, T. Imai, T. Itoh, T. Watanabe, and S. Kobayashi, Macromolecules, 33, 4155, 4982 (2000).
14. e) J. Sakamoto, T. Watanabe, Y. Ariga, and S. Kobayashi, Chem. Lett., 2001, 1180.
15. 3)O).
16. For comparison, enzymatic reaction of 1a was examined under the similar condition with those of 1b-1d, which completed in 2.5 h giving 2a with the following distribution; 63% of water-insoluble products (synthetic chitin), 1% of chitohexaose, 3% of chitotetraose, 1% of chitotriose, and 32% of chitobiose.
17. A. C. Terwisscha van Scheltinga, S. K. H. Kalk, A. Isogai, B. Henrissat, and B. W. Dijkstra, Biochemistry, 34, 15619 (1995).