Mechanism of the cyclopentane ring formation of allosamizoline, an aminocyclitol derivative of the chitinase inhibitor allosamidin

Tetrahedron Letters

Volumn 37, Issue 32, 1996, Pages 5711-5714

  Sakuda, Shohei ^a   Zhou, Ze Yang ^b   Takao, Hiroaki ^b   Yamada, Yasuhiro ^b  

^a UNIVERSITY OF TOKYO   (Japan)

^b OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALLOSAMIDIN; AMINOCYCLITOL;

ARTICLE; BIOSYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STREPTOMYCES;

STREPTOMYCES;

EID: 0030570896     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01207-5     Document Type: Article

References (21)

1. 1. Sakuda, S.; Isogai, A.; Matsumoto, S.; Suzuki, A. J. Antibiot., 1987, 40, 296-300.
2. 2. (a) Sakuda, S.; Nishimoto, Y; Ohi, M.; Watanabe, M.; Takayama, S.; Isogai, A.; Yamada, Y. Agric. Biol. Chem. 1990, 54, 1333-1335.
3. (b) Nishimoto, Y.; Sakuda, S.; Takayama, S.; Yamada, Y. J. Antibiot. 1991, 44, 716-722.
4. (c) Koga, D.; Isogai, A.; Sakuda, S.; Matsumoto, S.; Suzuki, A.; Kimura, S.; Ide, A. Agric. Biol. Chem. 1987, 51, 471-476.
5. (d) Butler, A. R.; O'Donnell, R. W.; Martin, V. J.; Gooday, G. W.; Stark, M. J. R. Eur. J. Biochem. 1991, 199, 483-488.
6. (e) Cabib, E.; Silverman, S. J.; Shaw, J. A. J. Gen. Microbiol. 1992, 138, 97-102.
7. (f) Sakuda, S.; Isogai, A.; Suzuki, A.; Yamada, Y. Actinomycetol., 1993, 7, 50-57.
8. 3. (a) Sakuda, S.; Isogai, A.; Matsumoto, S.; Suzuki, A.; Koseki, K. Tetrahedron Lett., 1986, 27, 2474-2478.
9. (b) Sakuda, S.; Isogai, A.; Makita, T.; Matsumoto, S.; Koseki, K.; Kodama, H.; Suzuki, A. Agric. Biol. Chem., 1987, 51, 3251-3259.
10. (c) Sakuda, S.; Isogai, A.; Matsumoto, S.; Suzuki, A.; Koseki, K,; Kodama, H.; Yamada, Y. Agric. Biol. Chem., 1988, 52, 1615-1617.
11. 4. Zhou, Z.; Sakuda, S.; Yamada, Y. J. Chem. Soc. Perkin Trans. 1, 1992, 1649-1652.
12. 5. (a) Weller, D. D.; Rinehard, Jr, K. L. J. Am. Chem. Soc., 1978, 100, 6757-6760.
13. (b) Flesch, G.; Rohmer, M. Eur. J. Biochem, 1988, 175, 405-411.
14. (c) Parry, R. J.; Bornemann, V.; Subramanian, R. J. Am. Chem. Soc., 1989, 111, 5819-5824.
15. 2H)as described in the following: Bundle, D. R.; Jennings, H. J.; Smith, I. C. R. Can. J. Chem., 1973, 51, 3812-3819.
16. 1H broad-band decoupling (pulse width = 45° , acquisition time = 4.096 s).
17. 2H2]-D-glucose, respectively, as described in the followings: (a) Nishida, Y.; Hori, H.; Ohrui, H.; Meguro, H. Carbohydr. Res., 1987, 170, 106-111.
18. (b) Mackie, W.; Perlin, A. S. Can. J. Chem., 1965, 43, 2645-2651.
19. (c) Moss, G. Arch. Biochem. Biophys., 1960, 90, 111-113.
20. 9. It's not clear why this increased value is much lower than that of di-labeled molecules of the labeled allosaminitol peracetate. If a non-stereospecific interconversion of 5 and 6, or an interconversion of 6 and its 6-carboxylic acid derivative or 7 and its 6-carboxylic acid derivative occurs during the formation of the cyclopentane ring in the pathway B, such a low deuterium incorporation onto C-6 of 2 might be observed.
21. 10. Jenkins, G. N.; Turner, N. J. Chem. Soc. Rev., 1995, 169-176.