Development of bifunctional photoactivatable benzophenone probes and their application to glycoside substrates

Biopolymers - Peptide Science Section

Volumn 90, Issue 4, 2008, Pages 526-536

  Qvit, Nir ^a,c   Monderer Rothkoff, Galya ^b   Ido, Ayelet ^b   Shalev, Deborah E ^a   Amster Choder, Orna ^b   Gilon, Chaim ^a  

^a HEBREW UNIVERSITY OF JERUSALEM   (Israel)

^b HEBREW UNIVERSITY   (Israel)

^c STANFORD UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

Arbutin; Benzophenone; Photoactivatable; Probes

Indexed keywords

ARSENIC COMPOUNDS; BACKPROPAGATION; BINDING ENERGY; BIOCHEMISTRY; CHLORINE COMPOUNDS; COENZYMES; COMPLEXATION; FLOW INTERACTIONS; LABELING; LIGANDS; RADIOISOTOPES; SUGARS; SUPRAMOLECULAR CHEMISTRY; SYNTHESIS (CHEMICAL);

ARBUTIN; BENZOPHENONE; BENZOPHENONE(BP); BIFUNCTIONAL; BIOLOGICAL STUDIES; CROSS LINKERS; GENERAL CHEMICAL; PHOTO AFFINITY; PHOTOACTIVATABLE; PHOTOAFFINITY LABELING; PHOTOLABELING; PROBES; PROTECTING GROUPS; PROTEIN COMPLEXES; PROTEIN INTERACTIONS; SOLID-PHASE SYNTHESIS; SPATIAL ARRANGEMENTS;

BINDING SITES;

ARBUTIN; AVIDIN; BENZOPHENONE DERIVATIVE; BIOTIN; N ETHYLMALEIMIDE;

ARTICLE; BINDING AFFINITY; BINDING SITE; CHEMICAL STRUCTURE; COMPLEX FORMATION; CROSS LINKING; LIGAND BINDING; PHOTOAFFINITY LABELING; PHOTOREACTIVITY; PROTEIN BINDING; PROTEIN PROTEIN INTERACTION; PROTEIN PURIFICATION; SOLID PHASE SYNTHESIS;

BENZOPHENONES; BIOTIN; ETHYLMALEIMIDE; GLYCOSIDES; MOLECULAR PROBES; PHOTOAFFINITY LABELS; PHOTOCHEMISTRY; PYRANS;

EID: 52949132198     PISSN: 00063525     EISSN: 10970282     Source Type: Journal    
DOI: 10.1002/bip.21010     Document Type: Article

References (56)

1. Singh, A.; Thornton, E. R.; Westheimer, F. H. J Biol Chem 1962, 237, 3006-3008.
2. Ruoho, A. E.; Kiefer, H.; Roeder, P. E.; Singer, S. J. Proc Natl Acad Sci USA 1973, 70, 2567-2571.
3. Galardy, R. E.; Craig, L. C.; Jamieson, J. D.; Printz, M. P. J Biol Chem 1974, 249, 3510-3518.
4. Robinette, D.; Neamati, N.; Tomer, K. B.; Borchers, C. H. Expert Rev Proteomics 2006, 3, 399-408.
5. Sinz, A. Mass Spectrom Rev 2006, 25, 663-682.
6. Son, C. D.; Sargsyan, H.; Hurst, G. B.; Naider, F.; Becker, J. M. J Pept Res 2005, 65, 418-426.
7. Wendeler, M.; Hoernschemeyer, J.; Hoffmann, D.; Kolter, T.; Schwarzmann, C.; Sandhoff, K. Eur J Biochem 2004, 271, 614-627.
8. Tomohiro, T.; Hashimoto, M.; Hatanaka, Y. Chem Rec 2005, 5, 385-395.
9. Vodovozova, E. L. Biochemistry (Moscow) 2007, 72, 1-20.
10. Fang, K.; Hashimoto, M.; Jockusch, S.; Turro, N. J.; Nakanishi, K. J Am Chem Soc 1998, 120, 8543-8544.
11. Brunner, J. Annu Rev Biochem 1993, 62, 483-514.
12. Duroux-Richard, I.; Vassault, P.; Subra, G.; Guichou, J. F.; Richard, E.; Mouillac, B.; Barberis, C.; Marie, J.; Bonnafous, J. C. Chem Biol 2005, 12, 15-24.
13. Kodadek, T.; Duroux-Richard, I.; Bonnafous, J. C. Trends Pharmacol Sci 2005, 26, 210-217.
14. Fancy, D. A.; Kodadek, T. Proc Natl Acad Sci USA 1999, 96, 6020-6024.
15. Sternbach, L. H. J Med Chem 1979, 22, 1-7.
16. Lehmann, T. E.; Muller, G.; Berkessel, A. J Org Chem 2000, 65, 2508-2516.
17. Farrell, I. S.; Toroney, R.; Hazen, J. L.; Mehl, R. A.; Chin, J. W. Nat Methods 2005, 2, 377-384.
18. Hino, N.; Okazaki, Y.; Kobayashi, T.; Hayashi, A.; Sakamoto, K.; Yokoyama, S. Nat Methods 2005, 2, 201-206.
19. Dorman, G.; Prestwich, G. D. Biochemistry 1994, 33, 5661-5673.
20. Branchini, B. R.; Magyar, R. A.; Marcantonio, K. M.; Newberry, K. J.; Stroh, J. G.; Hinz, L. K.; Murtiashaw, M. H. J Biol Chem 1997, 272, 19359-19364.
21. Tyagi, N. K.; Kinne, R. K. Anal Biochem 2003, 323, 74-83.
22. Guy, M. R.; Illarionov, P. A.; Gurcha, S. S.; Dover, L. G.; Gibson, K. J.; Smith, P. W.; Minnikin, D. E.; Besra, G. S. Biochem J 2004, 382, 905-912.
23. Otsuka, H.; Kijima, K. Chem Pharm Bull (Tokyo) 2001, 49, 699-702.
24. Peng, J.; Chen, P. Y.; Marchase, R. B.; Prestwich, G. D. Bioorg Med Chem Lett 2000, 10, 535-539.
25. Kitanov, G. M.; Nedialkov, P. T. Phytochemistry 2001, 57, 1237-1243.
26. Bellamy, F.; Horton, D.; Millet, J.; Picart, F.; Samreth, S.; Chazan, J. B. J Med Chem 1993, 36, 898-903.
27. Holman, G. D.; Karim, A. R.; Karim, B. Biochim Biophys Acta 1988, 946, 75-84.
28. Shen, R.; Inoue, T.; Forgac, M.; Porco, J. A., Jr.J Org Chem 2005, 70, 3686-3692.
29. Kato, E.; Howitt, R.; Dzyuba, S. V.; Nakanishi, K. Org Biomol Chem 2007, 5, 3758-3761.
30. Ahrends, R.; Kosinski, J.; Kirsch, D.; Manelyte, L.; Giron-Monzon, L.; Hummerich, L.; Schulz, O.; Spengler, B.; Friedhoff, P. Nucleic Acids Res 2006, 34, 3169-3180.
31. Leslie, J.; Williams, D. L.; Gorin, G. Anal Biochem 1962, 3, 257-263.
32. Smyth, D. G.; Blumenfeld, O. O.; Konigsberg, W. Biochem J 1964, 91, 589-595.
33. Gorin, G.; Martic, P. A.; Doughty, G. Arch Biochem Biophys 1966, 115, 593-597.
34. Brewer, C. F; Riehm, J. P. Anal Biochem 1967, 18, 248-255.
35. Griffiths, D. G.; Partis, M. D.; Sharp, R. N.; Beechey, R. B. Febs Lett 1981, 134, 261-263.
36. Olszewski, J. D.; Dorman, G.; Elliott, J. T.; Hong, Y.; Ahern, D. G.; Prestwich, G. D. Bioconjug Chem 1995, 6, 395-400.
37. Wilchek, M.; Bayer, E. A. Anal Biochem 1988, 171, 1-32.
38. Naider, F.; Yaron, A.; Ewenson, A.; Tallon, M.; Xue, C. B.; Srinivasan, J. V.; Eriotou-Bargiota, E.; Becker, J. M. Biopolymers 1990, 29, 237-245.
39. Rudnick, G.; Kaback, H. R. J Biol Chem 1975, 250, 6847-6851.
40. Kharat, A. S.; Mahadevan, S. Microbiology 2000, 146, 2039-2049.
41. el Hassouni, M.; Henrissat, B.; Chippaux, M.; Barras, F. J Bacteriol 1992, 174, 765-777.
42. Amster-Choder, O. Curr Opin Microbiol 2005, 8, 127-134.
43. Ambroise, Y.; Mioskowski, C.; Leblanc, G.; Rousseau, B. Bioorg Med Chem Lett 2000, 10, 1125-1127.
44. Bhatti, M. H.; Ali, S.; Huma, F.; Shahzadi, S. Turkish J Chemi 2005, 29, 463-476.
45. Khan, M. I.; Baloch, M. K.; Ashfaq, M. J Organomet Chem 2004, 689, 3370-3378.
46. Mantovani, G.; Lecolley, F.; Tao, L.; Haddleton, D. M.; Clerx, J.; Cornelissen, J.; Velonia, K. J Am Chem Soc 2005, 127, 2966-2973.
47. Tsubery, H.; Mironchik, M.; Fridkin, M.; Shechter, Y. J Biol Chem 2004, 279, 38118-38124.
48. Merrifield, R. B. J Am Chem Soc 1963, 85, 2149-2154.
49. Barlos, K.; Gatos, D.; Kallitsis, J.; Papaphotiu, G.; Sotiriu, P.; Yao, W. Q.; Schafer, W. Tetrahedron Lett 1989, 30, 3943-3946.
50. Alley, S. C.; Ishmael, F. T.; Jones, A. D.; Benkovic, S. J. J Am Chem Soc 2000, 122, 6126-6127.
51. Ferrari, J.; Terreaux, C.; Sahpaz, S.; Msonthi, J. D.; Wolfender, J. L.; Hostettmann, K. Phytochemistry 2000, 54, 883-889.
52. Ballell, L.; Alink, K. J.; Slijper, M.; Versluis, C.; Liskamp, R. M.; Pieters, R. J. Chembiochem 2005, 6, 291-295.
53. Yagur-Kroll, S.; Amster-Choder, O. J Biol Chem 2005, 280, 19306-19318.
54. Kauer, J. C.; Erickson-Viitanen, S.; Wolfe, H. R.,DeGrado, W. F. J Biol Chem 1986, 261, 10695-10700.
55. Kaiser, E.; Colescot, R. L.; Bossinge, C. D.; Cook, P. I. Anal Biochem 1970, 34, 595-598.
56. Christensen, T. Acta Chem Scand SerB-Org Chem Biochem 1979, 33, 763-766.