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Inhibition of prolyl oligopeptidase with a synthetic unnatural dipeptide

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Racys, Daurgidas Tomas, Rea, Dean, Fülöp, Vilmos and Wills, Martin. (2010) Inhibition of prolyl oligopeptidase with a synthetic unnatural dipeptide. Bioorganic & Medicinal Chemistry, Vol.18 (No.13). pp. 4775-4782. ISSN 0968-0896

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Official URL: http://dx.doi.org/10.1016/j.bmc.2010.05.012

Abstract

A new inhibitor, containing a linked proline-piperidine structure, for the enzyme prolyl oligopeptidase (POP) has been synthesised and demonstrated to bind covalently with the enzyme at the active site. This provides evidence that covalent inhibitors of POP do not have to be limited to structures containing five-membered N-containing heterocyclic rings.

Item Type: Journal Article
Subjects: Q Science > QD Chemistry
Q Science > QH Natural history > QH301 Biology
Divisions: Faculty of Science > Chemistry
Faculty of Science > Life Sciences (2010- ) > Biological Sciences ( -2010)
Library of Congress Subject Headings (LCSH): Enzyme inhibitors -- Research, Biosynthesis -- Research, Enzymes -- Regulation, Piperidine -- Research
Journal or Publication Title: Bioorganic & Medicinal Chemistry
Publisher: Elsevier
ISSN: 0968-0896
Date: 1 July 2010
Volume: Vol.18
Number: No.13
Page Range: pp. 4775-4782
Identification Number: 10.1016/j.bmc.2010.05.012
Status: Peer Reviewed
Access rights to Published version: Restricted or Subscription Access
Funder: Engineering and Physical Sciences Research Council (EPSRC)
References: 1. Lawandi, J.; Gerber-Lemaire, S.; Juillerat-Jeanneret, L.; Moitessier, N. J. Med. Chem. 2010, 53, ASAP (jm901104g). 2. (a) Fulop, V.; Bocskei, Z.; Polgar. L. Cell 1998, 94, 161-170. (b) Fulop, V.; Jones, D. T. Current Opinion in Structural Biology 1999, 9, 715–721. 3. Rea, D.; Fulop. V. Cell Biochemistry and Biophysics 2006, 44, 349-365. 4. Shan, L.; Mathews, I. I.; Khosla, C. PNAS, 2005, 102, 3599-3604. 5. Yoshimoto, T.; Kado, K.; Matsubara, F.; Koriyama, N.; Kaneto, H.; Tsuru. D. J. Pharmacobiodyn. 1987, 10, 730–735. 6. Maes, M.; Goossens, F.; Scharpe, S.; Calabrese, J.; Desnyder, R.; Meltzer, H. Y. Psychiatry Res. 1995, 58, 217–225. 7. Petit, A.; Barelli, H.; Morain, P.; Checler. F. Br. J. Pharmacol. 2000, 130, 1613–1617. 8. Grellier, P.; Vendeville, S.; Joyeau, R.; Bastos, I. M. D.; Drobecq, H.; Frappier, F.; Teixeira, A. R. L.; Schrevel, J.; Davioud-Charvet, E.; Sergheraert, C.; Santana. J. M. J. Biol. Chem. 2001, 276, 47078-47086. 9. Dahlin, N.; Bøgevig, A.; Adolfsson, H. Adv. Synth. Catal. 2004, 346, 1101 –1105. 10. Smith, K. M.; M. Miura, M.; Tabba, H. D. J. Org. Chem. 1983, 48, 4779-4781. 11. Goebel, T.; Ulmer, D.; Projahn, H.; Kloeckner, J.; Heller, E.; Glaser, M.; Ponte-Sucre, A.; Specht, S.; Sarite, S. R.; Hoerauf, A.; Kaiser, A.; Hauber, I.; Hauber, J.; Holzgrabe, U. Med. Chem. 2008, 51, 238-250. 12. Corey, E. J.; Venkateswarlu, A. J. Am. Chem. Soc. 1972, 94, 6190–6191. 13. Mota, A. J.; Chiaroni, A.; Langlois, N. Eur. J. Org. Chem. 2003, 4187-4198. 14. Gribkov, D. V.; Pastine, S. J.; Schnurch, M.; D. Sames, D. J. Am. Chem. Soc. 2007, 129, 11750-11755. 15. Li, B.; Berliner, M.; Buzon, R. ; Chiu, C. K.-F.; Colgan, S. T.; Kaneko, T.; Keene, N.; Kissel, W.; Le, T.; Leeman, K. R.; Marquez, B. ; Morris, R. ; Newell, L. ; Wunderwald, S. ; Witt, M. ; Weaver, J. ; Zhang, Z. ; Zhang, Z. J. Org. Chem. 2006, 71, 9045-9050. 16. Murray, A. J.; Parsons, P. J.; Hitchcock, P. Tetrahedron 2007, 63, 6485–6492. 17. Cohen, J. L.; Chamberlin, A. R. J. Org. Chem. 2007, 72, 9240-9247. 18. Padwa, A.; Wang, Q. J. Org. Chem. 2006, 71, 7391–7402. 19. Bohno, M.; Sugie, K.; Imase, H.; Yusof, Y. B.; Oishi, T.; Chida, N. Tetrahedron 2007, 63, 6977–6989. 20. Stockel-Maschek, A.; Stiebitz, B.; Koelsch, R.; Neubert, K. Anal. Biochem. 2003, 322, 60-67. 21. Macías, A.; Ramallal, A. M.; Alonso, E.; del Pozo, C.; González, J. J. Org. Chem. 2006, 71, 7721–7730. 22. Kondo, T.; Nekado, T.; Sugimoto, I.; Ochi, K.; Takai, S.; Kinoshita, A.; Hatayama, A.; Yamamoto, S.; Kishikawa, K.; Nakai, H.; Toda, M. Bioorg. Med. Chem. 2008, 16, 1613-1631. 23. Hargaden, G. C.; Muller-Bunz, H.; Guiry, P. J. Eur. J. Org. Chem., 2007, 4235-4243. 24. Guanti, G.; Riva, R. Tetrahedron: Asymmetry 2001, 12, 605–618. 25. Saltsman, I.; Goldberg, I.; Balasza, Y.; Z. Gross, Z. Tetrahedron Lett. 2007, 48, 239–244. 26. Chimni, S. S.; Mahajan, D. Tetrahedron: Asymmetry 2006, 17, 2108–2119. 27. T. Honma, K. Hayashi, T. Aoyama, N. Hashimoto, T. Machida, K. Fukasawa, T. Iwama, C. Ikeura, M. Ikuta, I. Suzuki-Takahashi, Y. Iwasawa, T. Hayama, S. Nishimura, and H. Morishima, J. Med. Chem., 2001, 44, 4615-4627. 28. Kanai, K.; Aranyi, P.; Bocskei, Z,; Ferenczy, G.; Harmat, V.; Simon, K.; Batori, S.; Naray-Szabo, G.; Hermecz, I. J. Med. Chem. 2008, 51, 7514-7522. 29. Collaborative Computational Project Number 4 (1994) The CCP4 suite: programs for protein crystallography, Acta Crystallogr., Sect. D 1994, 50, 760-763. 30. Murshudov, G. N.; Vagin, A. A.; Dodson, E. J. Acta Crystallogr., Sect. D: Biol. Crystallogr. 1997, 53, 240–255. 31. DeLano, W. L. The PyMOL User’s Manual 2002, DeLano Scientific, Palo Alto,CA. 32. Read, R. J. Acta Crystallogr., Sect. A. 1986, A42, 140–149. 33. Esnouf, R. M. J. Mol. Graphics Modell. 1997, 15, 133–138. 34. Calmes, M.; Escale, F.; Rolland, M.; Martinez, J. Tetrahedron: Asymmetry 2003, 14, 1685-1689. 35. Molander, G. A.; Romero, J. A. C. Tetrahedron 2005, 61, 2631–2643. 36. Stehl, A.; Seitz, G.; Schulz, K. Tetrahedron 2002, 58, 1343-1354. 37. Sanchez-Sancho F.; Herradon, B.; Molander, G. A.; Romero, J. A. C. Tetrahedron: Asymmetry 2005, 9, 2631–2643. 38 Hart, D.J.; Li, J.; Wu, W.; Kozikowski, A. P. J. Org. Chem. 1997, 62, 5023-5033. 39. Fletcher, D. A.; McMeeking, R. F.; Parkin, D. J. Chem. Inf. Comput. Sci. 1996, 36, 746.
URI: http://wrap.warwick.ac.uk/id/eprint/3307

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