Fmoc-based solid-phase synthesis of GPR54-agonistic pentapeptide derivatives containing alkene- and fluoroalkene-dipeptide isosteres

Biopolymers - Peptide Science Section

Volumn 88, Issue 2, 2007, Pages 272-278

  Tomita, Kenji ^a   Narumi, Tetsuo ^a   Niida, Ayumu ^a   Oishi, Shinya ^a   Ohno, Hiroaki ^a   Fujii, Nobutaka ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

(E) fluoroalkene dipeptide isostere; (Z) alkene dipeptide isostere; Fmoc based SPPS; GPR54 agonist

Indexed keywords

FADI BIOISOSTERISM; GPR54 AGONISTIC PENTAPEPTIDE DERIVATIVES; PEPTIDE BOND; SOLID PHASE PEPTIDE SYNTHESIS (SPPS);

AMIDES; BIOACTIVITY; CONFORMATIONS; FLUORINE COMPOUNDS; OLEFINS; ORGANIC ACIDS; SYNTHESIS (CHEMICAL);

PEPTIDES;

ALKENE; ALKENE DERIVATIVE; FLUOROALKENE; G PROTEIN COUPLED RECEPTOR 54; PENTAPEPTIDE; UNCLASSIFIED DRUG;

CHEMICAL REACTION; CONFERENCE PAPER; PEPTIDE SYNTHESIS; PROTEIN STRUCTURE; SOLID; SYNTHESIS;

ALKENES; AMINO ACIDS; DIPEPTIDES; FLUORENES; HUMANS; MOLECULAR STRUCTURE; OLIGOPEPTIDES; RECEPTORS, G-PROTEIN-COUPLED;

EID: 34247478101     PISSN: 00063525     EISSN: 10970282     Source Type: Journal    
DOI: 10.1002/bip.20676     Document Type: Conference Paper

References (42)

1. Fujii, N.; Oishi, S.; Hiramatsu, K.; Araki, T.; Ueda, S.; Tamamura, H.; Otaka, A.; Kusano, S.; Terakubo, S.; Nakashima, H.; Broach, J. A.; Trent, J. O.; Wang, Z.; Peiper, S. C. Angew Chem Int Ed Engl 2003, 42, 3251-3253.
2. Tamamura, H.; Hiramatsu, K.; Kusano, S.; Terakubo, S.; Yamamoto, N.; Trent, J. O.; Wang, Z.; Peiper, S. C.; Nakashima, H.; Otaka, A.; Fujii, N. Org Biomol Chem 2003, 1, 3656-3662.
3. Boyle, R. G.; Downham, R.; Ganguly, T.; Humphries, J.; Smith, J.; Travers, S. J Pept Sci 2005, 11, 161-165.
4. Mazarguil, H.; Gouardères, C.; Tafani, J.-A. M.; Marcus, D.; Kotani, M.; Mollereau, C.; Roumy, M.; Zajac, J.-M. Peptides 2001, 22, 1471-1478.
5. Dugave, C.; Demange, L. Chem Rev 2003, 103, 2475-2532.
6. Oishi, S.; Kamano, T.; Niida, A.; Odagaki, Y.; Hamanaka, N.; Yamamoto, M.; Ajito, K.; Tamamura, H.; Otaka, A.; Fujii, N. J Org Chem 2002, 67, 6162-6173.
7. Wipf, P.; Xiao, J. Org Lett 2005, 7, 103-106.
8. Xiao, J.; Weisblum, B.; Wipf, P. J Am Chem Soc 2005, 127, 5742-5743.
9. Abraham, R. J.; Ellison, S. L. R.; Schonholzer, P.; Thomas, W. A. Tetrahedron 1986, 42, 2101-2110.
10. Ibuka, T.; Habashita, H.; Otaka, A.; Fujii, N.; Oguchi, Y.; Uyehara, T.; Yamamoto, Y. J Org Chem 1991, 56, 4370-4382.
11. Ibuka, T.; Taga, T.; Habashita, H.; Nakai, K.; Tamamura, H.; Fujii, N.; Chounan, Y.; Nemoto, H.; Yamamoto, Y. J Org Chem 1993, 58, 1207-1214.
12. Wipf, P.; Fritch, P. C. J Org Chem 1994, 59, 4875-4886.
13. Wipf, P.; Henninger, T. C. J Org Chem 1997, 62, 1586-1587.
14. Daly, M. J.; Ward, R. A.; Thompson, D. F.; Procter, G. Tetrahedron Lett 1995, 36, 7545-7548.
15. Welch, J. T.; Lin, J. Tetrahedron 1996, 52, 291-304.
16. Otaka, A.; Watanabe, J.; Yukimasa, A.; Sasaki, Y.; Watanabe, H.; Kinoshita, T.; Oishi, S.; Tamamura, H.; Fujii, N. J Org Chem 2004, 69, 1634-1645.
17. Nakamura, Y.; Okada, M.; Koura, M.; Tojo, M.; Saito, A.; Sato, A.; Taguchi, T. J Fluorine Chem 2006, 127, 627-636.
18. Synthesis of (E)-FADIs has been also reported (Ref. 19 and 20).
19. Allmendinger, T.; Furet, P.; Hungerbühler, E. Tetrahedron Lett 1990, 31, 7297-7300.
20. Boros, L. G.; Corte, B. D.; Gimi, R. H.; Welch, J. T.; Wu, Y.; Handschumacher, R. E. Tetrahedron Lett 1994, 35, 6033-6036.
21. Tamamura, H.; Hiramatsu, K.; Ueda, S.; Wang, Z.; Kusano, S.; Terakubo, S.; Trent, J. O.; Peiper, S. C.; Yamamoto, N.; Nakashima, H.; Otaka, A.; Fujii, N. J Med Chem 2005, 48, 380-391.
22. Christos, T. E.; Arvanitis, A.; Cain, G. A.; Johnson, A. L.; Pottorf, R. S.; Tam, S. W.; Schmidt, W. K. Bioorg Med Chem Lett 1993, 3, 1035-1040.
23. Allmendinger, T.; Felder, E.; Hungerbuhler, E. Tetrahedron Lett 1990, 31, 7301-7304.
24. Bartlett, P. A.; Otake, A. J Org Chem 1995, 60, 3107-3111.
25. Lin, J.; Toscano, P. J.; Welch, J. T. Proc Natl Acad Sci USA 1998, 95, 14020-14024.
26. Oishi, S.; Miyamoto, K.; Niida, A.; Yamamoto, M.; Ajito, K.; Tamamura, H.; Otaka, A.; Kuroda, Y.; Asai, A.; Fujii, N. Tetrahedron 2006, 62, 1416-1424.
27. Niida, A.; Tomita, K.; Mizumoto, M.; Tanigaki, H.; Terada, T.; Oishi, S.; Otaka, A.; Inui, K.; Fujii, N. Org Lett 2006, 8, 613-616.
28. Boucard, V.; Sauriat-Dorizon, H.; Guibé, F. Tetrahedron 2002, 58, 7275-7290.
29. Honda, T.; Wakabayashi, H.; Kanai, K. Chem Pharm Bull 2002, 50, 307-308.
30. Kutzleb, G.; Busmann, A.; Wendland, M.; Maronde, E. Curr Protein Pept Sci 2005, 6, 265-278.
31. Tyndall, J. D. A.; Pfeiffer, B.; Abbenante, G.; Fairlie, D. P. Chem Rev 2005, 105, 793-826.
32. Kanosue, Y.; Kojima, S.; Ohkata, K. J Phys Org Chem 2004, 17, 448-457.
33. Lee, D. K.; Nguyen, T.; O'Neill, G. P.; Cheng, R.; Liu, Y.; Howard, A. D.; Coulombe, N.; Tan, C. P.; Tang-Nguyen, A.-T.; George, S. R.; O'Dowd, B. F. FEBS Lett 1999, 446, 103-107.
34. Tomita, K.; Niida, A.; Oishi, S.; Ohno, H.; Cluzeau, J.; Navenot, J.-M.; Wang, Z.; Peiper, S. C.; Fujii, N. Bioorg Med Chem 2006, 14, 7595-7603.
35. Ohtaki, T.; Shintani, Y.; Honda, S.; Matsumoto, H.; Hori, A.; Kanehashi, K.; Terao, Y.; Kumano, S.; Takatsu, Y.; Masuda, Y.; Ishibashi, Y.; Watanabe, T.; Asada, M.; Yamada, T.; Suenaga, M. Kitada, C.; Usuki, S.; Kurokawa, T.; Onda, H.; Nishimura, O.; Fujino, M. Nature 2001, 411, 613-617.
36. Hori, A.; Honda, S.; Asada, M.; Ohtaki, T.; Oda, K.; Watanabe, T.; Shintani, Y.; Yamada, T.; Suenaga, M.; Kitada, C.; Onda, H.; Kurokawa, T.; Nishimura, O.; Fujino, M. Biochem Biophys Res Commun 2001, 286, 958-963.
37. Stathatos, N.; Bourdeau, I.; Espinosa, A. V.; Saji, M.; Vasko, V. V.; Burman, K. D.; Stratakis, C. A.; Ringel, M. D. J Clin Endocrinol Metab 2005, 90, 5432-5440.
38. Dungan, H. M.; Clifton, D. K.; Steiner, R. A. Endocrinology 2006, 147, 1154-1158.
39. Seminara, S. B. Front Neuroendocrinol 2005, 26, 131-138.
40. Murphy; K. G. J. Neuroendocrinol 2005, 17, 519-525.
41. Schölkopf, U.; Hartwig, W.; Pospischil, K.-H.; Kehne, H. Synthesis 1981, 966-969.
42. Garbe, D.; Sieber, S. A.; Bandur, N. G.; Koert, U.; Marahiel, M. A. ChemBioChem 2004, 5, 1000-1003.