Cross-linking chemistry and biology: Development of multifunctional photoaffinity probes

Chemical Record

Volumn 5, Issue 6, 2005, Pages 385-395

  Tomohiro, Takenori ^a   Hashimoto, Makoto ^b   Hatanaka, Yasumaru ^a  

^a UNIVERSITY OF TOYAMA   (Japan)

^b OBIHIRO UNIVERSITY OF AGRICULTURE AND VETERINARY MEDICINE   (Japan)

Author keywords

Biotinylation; Chemical biology; Drug screening; Photoaffinity labeling; Proteomics

Indexed keywords

DIAZOMETHANE;

CHEMISTRY; PHOTOAFFINITY LABELING; PROTEIN CONFORMATION; REVIEW;

DIAZOMETHANE; PHOTOAFFINITY LABELS; PROTEIN CONFORMATION;

EID: 33645507015     PISSN: 15278999     EISSN: 15280691     Source Type: Journal    
DOI: 10.1002/tcr.20058     Document Type: Review

References (51)

1. (a) Hatanaka, Y.; Sadakane, Y. Curr Topics Med Chem 2002, 2, 271-8;
2. (b) Kotzyba-Hibert, F.; Kapfer, I.; Goeldner, M. Angew Chem Int Ed Engl 1995, 34, 1296-1312;
3. (c) Brunner, J. Ann Rev Biochem 1993, 62, 483-514;
4. (d) Sadakane, Y.; Hatanaka, Y. In Chemical Genomics: Advances in Drug Discovery and Functional Genomics Applications, Ed F. Darvas, A. Guttman, G. Dormán; Marcel Dekker: New York, 2004; Ch 6.
5. Yoshida, E.; Nakayama, H.; Hatanaka, Y.; Kanaoka, Y. Chem Pharm Bull 1990, 38, 982-7.
6. Bayer, E. A.; Wilchek, M. J Chromatogr 1990, 510, 3-11.
7. (a) Hatanaka, Y.; Hashimoto, M.; Kanaoka, Y. J Am Chem Soc 1998, 120, 453-4;
8. (b) Hashimoto, M.; Hatanaka, Y. Chem Pharm Bull 1999, 47, 667-71.
9. Hatanaka, Y.; Ishiguro, M.; Hashimoto, M.; Gastinel, L. N.; Nakagomi, K. Bioorg Med Chem Lett 2001, 11, 411-13.
10. Rühl, T.; Volke, D.; Stembera, K.; Hatanaka, Y.; Hennig, H.; Schumer, F.; Welzel, P. Chem Commun 2002, 1630-1.
11. Hashimoto, M.; Hatanaka, Y.; Yang, J.; Dhesi, J.; Holman, G. D. Carbohydr Res 2001, 331, 119-27.
12. Konoki, K.; Sugiyama, N.; Murata, M.; Tachibana, K.; Hatanaka, Y. Tetrahedron 2000, 56, 9003-14.
13. Hatanaka, Y.; Nakayama, H.; Kanaoka, Y. Rev Heteroatom Chem 1996, 14, 213-43.
14. (a) Holman, G. D.; Parkar, B. A.; Midgley, P. J. W. Biochim Biophys Acta 1986, 855, 115-26 (1986);
15. (b) Holman, G. D.; Karim, A. R.; Karim, B. Biochim Biophys Acta 1988, 946, 75-84;
16. (c) Holman, G. D.; Kozka, I. J.; Clark, A. E.; Flower, C. J.; Saltis, J.; Habberfield, A. D.; Simpson, I. A.; Cushman, S. W. J Biol Chem 1990, 265, 18172-9.
17. Brunner, J.; Senn, H.; Richards, F. M. J Biol Chem 1980, 255, 3313-18.
18. Hatanaka, Y.; Hashimoto, M.; Kurihara, H.; Nakayama, H.; Kanaoka, Y. J Org Chem 1994, 59, 383-7.
19. Hashimoto, M.; Kanaoka, Y.; Hatanaka, Y. Heterocycles 1997, 46, 119-22.
20. Hatanaka, Y.; Hashimoto, M.; Nakayama, H.; Kanaoka, Y. Chem Pharm Bull 1994, 42, 826-31.
21. Hashimoto, M.; Nabeta, K.; Murakami, K. Bioorg Med Chem Lett 2003, 13, 1531-3.
22. Hashimoto, M.; Hatanaka, Y.; Nabeta, K. Bioorg Med Chem Lett 2000, 10, 2481-3.
23. Kempin, U.; Kanaoka, Y.; Hatanaka, Y. Heterocycles 1998, 49, 465-8.
24. Shigenari, T.; Hakogi, T.; Katsumura T. Chem Lett 2004, 33, 594-5.
25. Hashimoto, M.; Komano, T.; Hatanaka, Y. Unpublished results.
26. Gilbert, B. A.; Rando, R. R. J Am Chem Soc 1995, 117, 8061-6.
27. Hatanaka, Y.; Hashimoto, M.; Kanaoka, Y. Bioorg Med Chem 1994, 2, 1367-73.
28. (a) Hatanaka, Y.; Hashimoto; M.; Jwa Hidari, K. I.-P.; Sanai, Y.; Tezuka, Y.; Nagai, Y.; Kanaoka, Y. Chem Pharm Bull 1996, 44, 1111-14;
29. (b) Hatanaka, Y.; Hashimoto, M.; Nishihara, S.; Narimatsu, H.; Kanaoka, Y. Carbohydr Res 1996, 294, 95-108.
30. Hatanaka, Y.; Kempin, U.; Park, J.-J. J Org Chem 2000, 65, 5639-43.
31. Ueda, H.; Fukushima, H.; Hatanaka, Y.; Ogawa, H. Biochem J 2004, 382, 821-9.
32. Kitamura, N.; Ikekita, M.; Sato, T.; Akimoto, Y.; Hatanaka, Y.; Kawakami, H.; Inomata, M.; Furukawa, K. Proc Natl Acad Sci USA 2005, 102, 2796-801.
33. Kinoshita, T.; Cano-Delgado, A.; Seto, H.; Hiranuma, S.; Fujioka, S.; Yoshida, S.; Chory, J. Nature 2005, 433, 167-71.
34. Hashimoto, M.; Yang, J.; Holman, G. D. ChemBioChem 2001, 2, 52-9.
35. Schäfer, H.-J.; Schuhen, A. Biol Res 1996, 29, 31-46.
36. Kauer, J. C.; Erickson-Viitanen, S.; Wolfe, Jr. H. R.; DeGrado, W. F. J Biol Chem 1986, 261, 10695-700.
37. Falchetto, R.; Vorherr, T.; Brunner, J.; Carafoli, E. J Biol Chem 1991, 266, 2930-6.
38. Hashimoto, M.; Hatanaka, Y.; Sadakane, Y.; Nabeta, K. Bioorg Med Chem Lett 2002, 12, 2507-10.
39. (a) Kauer, J. C.; Erickson-Viitanen, S.; Wolfe, H. R. J Biol Chem 1986, 261, 10695-700;
40. (b) Chin, J. W.; Martin, A. B.; King, D. S.; Wang, L.; Schultz, P. G. Proc Natl Acad Sci USA 2002, 99, 11020-4.
41. Park, J.-J.; Sadakane, Y.; Masuda, K.; Tomohiro, T.; Nakano, T.; Hatanaka, Y. ChemBioChem 2005, 6, 814-8.
42. Hashimoto, M.; Okamoto, S.; Nabeta, K.; Hatanaka Y. Bioorg Med Chem Lett 2004, 14, 2447-50.
43. Hashimoto, M.; Hatanaka, Y. Chem Pharm Bull 2004, 52, 1385-6.
44. Hashimoto, M.; Komano, T.; Nabeta, K.; Hatanaka, Y. Chem Pharm Bull 2005, 53, 140-2.
45. Kanoh, N.; Kumashiro, S.; Simizu, S.; Kondoh, Y.; Hatakeyama, S.; Tashiro, H.; Osada, H. Angew Chem Int Ed Engl 2003, 42, 5584-7.
46. Hatanaka, Y.; Tomohiro, T. Patent Pending.
47. Kang, J. J.; Tarcsafalvi, A.; Carlos, A. D.; Fujimoto, E.; Shahrokh, Z.; Thevenin, B. J. M.; Shohet, S. B.; Ikemoto, I. Biochemistry 1992, 31, 3288-93.
48. Hamachi, I.; Nagase, T.; Shinkai, S. J Am Chem Soc 2000, 122, 12065-6.
49. Chin, J. W.; Schultz, P. G. ChemBioChem 2002, 3, 1135-7.
50. Galzi, J.; Revah, F.; Bouet, F.; Menez, A.; Goeldner, M.; Hirth, C.; Changeux, J. Proc Natl Acad Sci USA 1991, 88, 5051-5.
51. Kanamori, T.; Nishikawa, S.; Shin, I.; Schultz, P. G.; Endo, T. Proc Natl Acad Sci USA 1997, 94, 485-90.