Toward the selective inhibition of G proteins: Total synthesis of a simplified YM-254890 analog

Organic Letters

Volumn 17, Issue 9, 2015, Pages 2270-2273

  Rensing, Derek T ^a   Uppal, Sakshi ^a   Blumer, Kendall J ^b   Moeller, Kevin D ^a  

^a WASHINGTON UNIVERSITY   (United States)

^b WASHINGTON UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPEPTIDE; GUANINE NUCLEOTIDE BINDING PROTEIN; YM-254890;

AGONISTS; CHEMICAL STRUCTURE; CHEMISTRY; SIGNAL TRANSDUCTION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

CRYSTALLOGRAPHY, X-RAY; GTP-BINDING PROTEINS; MOLECULAR STRUCTURE; PEPTIDES, CYCLIC; SIGNAL TRANSDUCTION;

EID: 84928901863     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/acs.orglett.5b00944     Document Type: Article

References (21)

1. Kimple, A. J.; Bosch, D. E.; Gigue, P. M.; Siderovski, D. P. Pharmacol Rev. 2011, 63, 728-749
2. Lagerström, M. C.; Schiöth, H. B. Nat. Rev. Drug Discovery 2008, 7, 339-57
3. Wettschureck, N.; Offermanns, S.; Mammalian, G. Physiol. Rev. 2005, 85, 1159-1204
4. Peptide, R. C.; Scheuring, J.; Schramm, V. L. Biochemistry 1997, 2960, 8215-8223
5. Locht, C.; Antoine, R. Biochimie 1995, 77, 333-340
6. Komatsu, M.; McDermott, A. M.; Gillison, S. L.; Sharp, G. W. G. Endocrinology 1995, 136, 1857-1863
7. Katada, T.; Ui, M. Proc. Natl. Acad. Sci. U.S.A. 1982, 79, 3129-3133
8. Taniguchi, M.; Nagai, K.; Arao, N.; Kawasaki, T.; Saito, T.; Moritani, Y.; Takasaki, J.; Hayashi, K.; Fujita, S.; Tsukamoto, S. J. Antibiot. (Tokyo) 2003, 56, 358-363
9. Nishimura, A.; Kitano, K.; Takasaki, J.; Taniguchi, M.; Mizuno, N.; Tago, K.; Hakoshima, T.; Itoh, H. Proc. Natl. Acad. Sci. U.S.A. 2010, 107, 13666-13671
10. Taniguchi, M.; Suzumura, K.; Nagai, K.; Kawasaki, T.; Takasaki, J.; Sekiguchi, M.; Moritani, Y.; Saito, T.; Hayashi, K.; Fujita, S.; Tsukamoto, S.; Suzuki, K. Bioorg. Med. Chem. Lett. 2004, 12, 3125-3133
11. Takasaki, J.; Saito, T.; Taniguchi, M.; Kawasaki, T.; Moritani, Y.; Hayashi, K.; Kobori, M. J. Biol. Chem. 2004, 279, 47438-47445
12. Kawasaki, T.; Taniguchi, M.; Moritani, Y.; Uemura, T.; Shigenaga, T.; Takamatsu, H. Thromb. Haemost. 2005, 94, 184-192
13. Uemura, T.; Kawasaki, T.; Taniguchi, M.; Moritani, Y.; Hayashi, K.; Saito, T.; Takasaki, J.; Uchida, W.; Miyata, K. Br. J. Pharmacol. 2006, 148, 61-9
14. For a synthesis of the related YM-280193 platelet aggregation inhibitor, see: Kaur, H.; Harris, P. W. R.; Little, P. J.; Brimble, M. A. Org. Lett. 2015, 17, 492-495
15. Kazmaier, U.; Mues, H.; Krebs, A. Chem.-Eur. J. 2002, 8, 1850-1855
16. Makino, K.; Okamoto, N.; Hara, O.; Hamada, Y. Tetrahedron: Asymmetry 2001, 12, 1757-1762
17. Benoiton, N. L. Chemistry of Peptide Synthesis; Taylor & Francis: Boca Raton, FL, 2006; pp 7-11.
18. For a review of cyclic peptides synthesized by metathesis reactions, see: Wakchaure, S.; Einsiedel, J.; Waibel, R.; Gmeiner, P. Synthesis 2012, 44, 2682-2694
19. Chidiac, P.; Markin, V. S.; Ross, E. M. Biochem. Pharmacol. 1999, 58, 39-48
20. Greentree, W. K.; Linder, M. E. Methods Mol. Biol. 2004, 237, 3-20
21. Zaima, K.; Deguchi, J.; Matsuno, Y.; Kaneda, T.; Hirasawa, Y.; Morita, H. J. Nat. Med. 2013, 67, 196-201