Deamination of 9-(hydroxymethylated cycloalkyl)-9H-adenines (carbocyclic adenine nucleosides) by adenosine deaminase: Effect of high-pressure upon deamination rate and enantioselectivity

Nucleosides and Nucleotides

Volumn 15, Issue 1-3, 1996, Pages 631-647

  Katagiri, Nobuya ^a   Ito, Yumiko ^a   Shiraishi, Takuya ^a   Maruyama, Tokumi ^b   Sato, Yoshiko ^b   Kaneko, Chikara ^a  

^a TOHOKU UNIVERSITY   (Japan)

^b TOKUSHIMA BUNRI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ADENOSINE DEAMINASE; CARBOCYCLIC NUCLEOSIDE; CARBOVIR;

ARTICLE; ENANTIOMER; ENZYME ACTIVITY; ENZYME SPECIFICITY; TECHNIQUE;

EID: 0029962143     PISSN: 07328311     EISSN: None     Source Type: Journal    
DOI: 10.1080/07328319608002411     Document Type: Article

References (21)

1. Part 38 in the series "Synthesis of Nucleosides and Related Compounds". For Part 37, see Katagiri, N.; Makino, S.; Kaneko, C. Chem. Pharm. Bull., 1995, 43, 884.
2. Part 38 in the series "Synthesis of Nucleosides and Related Compounds". For Part 37, see Katagiri, N.; Makino, S.; Kaneko, C. Chem. Pharm. Bull., 1995, 43, 884.
3. Agarwal, P.; Sager, S. M.; Parks, R. E. Biochem. Pharmacol., 1978, 24, 693.
4. Martin, D. W.; Gelfand, E. W. Ann. Rev. Biochem., 1981, 50, 845.
5. a) Cowan, M. J.; Brady, R. O.; Widder, K. J. Proc. Natl. Acad. Sci. U.S.A., 1983, 83, 1089;
6. b) Gan, T. E.; Dadonna, P. E.; Mitchel, B. S. Blood, 1987, 69, 1376.
7. Wilson, D. K.; Rudolph, F. B.; Quiocho, F. A. Science, 1991, 25, 1278.
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10. Katagiri, N.; Shiraishi, T.; Toyota, A.; Sato, H.; Kaneko, C.; Aikawa, T. Chem. Pharm. Bull., 1993, 41, 1027.
11. Katagiri, N.; Sato, H.; Kaneko, C. Chem. Pharm. Bull., 1990, 38, 3184.
12. Honjo, M.; Maruyama, T.; Sato, Y.; Horii, T. Chem. Pharm. Bull., 1989, 37, 1413.
13. Norbeck, D. W.; Plattner, J. J.; Rosen, T. J.; Pariza, R. J.; Sowin, T. J.; Garmaise, D. L.; Hannick, S. M. Eur. Pat. Appl. EP366, 059, 1990. Chem. Abst., 1990, 113, 212577V.
14. Vince, R.; Hua, M.; Brownell, J.; Daluge, S.; Lee, F.; Shannon, W.; Lavelle, G.; Qualls, J.; Weislow, O.; Kiser, R.; Canonico, P.; Schultz, R.; Narayanan, V.; Mayo, J.; Shoemaker, R.; Boyd, M. Biochem. Biophys. Res. Commun., 1988, 156, 1046.
15. Slusarchyk, W. A.; Young, M. G.; Bisacchi, G. S.; Hockstein, D. R.; Zahler, R. Tetrahedron Lett., 1989, 30, 6453.
16. Kaneko, C.; Katagiri, N.; Nomura, M.; Sato, H.; Israel J. Chem., 1991, 31, 247.
17. a) Toyota, A.; Habutani, C.; Katagiri, N.; Kaneko, C.; Tetrahedron Lett., 1994, 35, 5665;
18. b) See also, Flymn, D. L.; Zelle, R. E. Grieco, P. A. J. Org. Chem., 1983, 48, 2424.
19. Compound 15 has been synthesized by the reaction of chlorosulfonyl isocyanate with 1,3-cyclohexadiene. Malpass, J. R.; Tweddle, N. J. J. Chem. Soc., Parkin Trans. I, 1976, 874. We obtained 15 from the [4+2] cycloaddition of benzenesulfonyl cyanide with 1,3- cyclohexadiene, followed by hydrolysis.
20. Bisacchi, G. S.; Braitman, A.; Cianci, C. W.; Clark, J. M.; Field, A. K.; Hagen, M. E.; Hockstein, D. R.; Malley, M. F.; Mitt, T.; Slusarchk, W. A.; Sundeen, J. E.; Terry, B. J.; Tuomari, A. V.; Weaver, E. R.; Young, M. G.; Zahler, R. J. Med. Chem., 1991, 34, 1415.
21. Compound 11 and benzenesulfonyl cyanide were provided by Kuraray Co., Ltd.