Synthesis of a doubly labelled concanamycin derivative for ATPase binding studies

European Journal of Organic Chemistry

Volumn , Issue 23, 2001, Pages 4525-4532

  Ingenhorst, Gudrun ^a   Bindseil, Kai Uwe ^a   Boddien, Claudia ^a   Dröse, Stefan ^b   Gaßel, Michael ^b   Altendorf, Karlheinz ^b   Zeeck, Axel ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

^b UNIVERSITY OF OSNABRÜCK   (Germany)

Author keywords

Enzymes; Iodine; Natural products; Photoaffinity labelling

Indexed keywords

23 IODO 9 O [4 (TRIFLUOROETHYLDIAZIRINYL)BENZOYL] 21,23 DIDEOXYCONCANOLIDE A I 125; ADENOSINE TRIPHOSPHATASE; CONCANAMYCIN A; UNCLASSIFIED DRUG;

ARTICLE; BINDING SITE; COMPLEX FORMATION; DERIVATIZATION; DRUG RECEPTOR BINDING; DRUG STABILITY; PHOTOAFFINITY LABELING; RADIOACTIVITY; SYNTHESIS;

EID: 0035215493     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200112)2001:23<4525::aid-ejoc4525>3.0.co;2-s     Document Type: Article

References (26)

1. C. Boddien, J. Gerber-Nolte, A. Zeeck, Liebigs Ann. 1996, 1381-1384.
2. K. U. Bindseil, A. Zeeck, Liebigs Ann. Chem. 1994, 305-312.
3. E. J. Bowman, A. Siebers, K. Altendorf, Proc. Natl. Acad. Sci. USA 1988, 85, 7972-7976.
4. S. Dröse, K. U. Bindseil, E. J. Bowman, A. Siebers, A. Zeeck, K. Altendorf, Biochemistry 1993, 32, 3902-3906.
5. J.-T. Woo, Y. Ohba, K. Tagami, K. Sumitani, K. Yamaguchi, T. Tsuji, Biol. Pharm. Bull. 1996, 19, 297-299.
6. S. Gagliardi, P. A. Gatti, P. Belfiore, A. Zocchetti, G. D. Clarke, C. Farina, J. Med. Chem. 1998, 41, 1883-1893.
7. J. W. Westley, C. M. Liu, L. H. Sello, R. H. Evans, N. Troupe, J. F. Blount, A. M. Chiu, L. J. Todaro, P. A. Miller, J. Antibiot. 1984, 37, 1738-1740.
8. T. Manabe, T. Yoshimori, N Henomatsu, Y. Tashiro, J. Cell. Physiol. 1993, 157, 445-452.
9. S. Dröse, K. Altendorf, J. Exp. Biol. 1997, 200, 1-8.
10. J. Zhang, Y. Feng, M. Forgac, J. Biol. Chem. 1994, 269, 23518-23523.
11. B. P. Crider, X.-S. Xie, D. K. Stones, J. Biol. Chem. 1994, 269, 17379-17381.
12. K. U. Bindseil, PhD Dissertation 1993, Universität Göttingen.
13. C. Boddien, PhD Dissertation 1995, Universität Göttingen.
14. K. U. Bindseil, A. Zeeck, J. Org. Chem. 1993, 58, 5487-5492.
15. S. Dröse, C. Boddien, M. Gaßel, G. Ingenhorst, A. Zeeck, K. Altendorf, Biochemistry 2001, 40, 2816-2825.
16. K. Altendorf, M. Gassel, W. Puppe, T. Möllenkamp, A. Zeeck, C. Boddien, K. Fendler, E. Bamberg, S. Dröse, Acta Physiol. Scand. 1998, 643, 137-146.
17. H. Kinashi, K. Someno, K. Sakaguchi, J. Antibiot. 1984, 37, 1333-1343.
18. K. U. Bindseil, A. Zeeck, Helv. Chim. Acta 1993, 76, 150-157.
19. J. Brunner, H. Senn, F. M. Richards, J. Biol. Chem. 1980, 255, 3313-3317.
20. D. A. Horne, A. Jordan, Tetrahedron Lett. 1978, 16, 1357-1358.
21. B. Neises, W. Steglich, Angew. Chem. 1978, 90, 556-557;
22. Angew. Chem. Int. Ed. Engl. 1978, 17, 552-553.
23. J.-H. Cho, C. Djerassi, J. Org. Chem. 1987, 52, 4517-4521.
24. [15] 11b was mentioned as possessing a 23-epi configuration. This should now be changed on the basis of better resolved NMR spectra.
25. E. Pretsch et. al., Strukturaufklärung organischer Verbindungen, Springer Verlag Berlin, 1990.
26. M. Huss, M. Gassel, G. Ingenhorst, S. Dröse, S. König, A. Zeeck, K. Altendorf, H. Wieczorek, Biochemistry, submitted.