Double-sided α-helix mimetics

Tetrahedron

Volumn 68, Issue 23, 2012, Pages 4501-4505

  Thompson, Sam ^a   Vallinayagam, Ramakrishnan ^b   Adler, Marc J ^a,b,c   Scott, Richard T W ^a   Hamilton, Andrew D ^a,b  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b YALE UNIVERSITY   (United States)

^c NORTHERN ILLINOIS UNIVERSITY   (United States)

Author keywords

Foldamer; Helical structure; Peptidomimetic; Protein protein interaction; Proteomimetic

Indexed keywords

BENZAMIDE DERIVATIVE; OLIGOMER; PEPTIDOMIMETIC AGENT;

ALPHA HELIX; ARTICLE; HYDROGEN BOND; MOLECULAR MIMICRY; PRIORITY JOURNAL;

EID: 84860678142     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2011.11.010     Document Type: Article

References (34)

1. S. Jones, and J.M. Thornton Proc. Natl. Acad. Sci. U.S.A. 93 1996 13 20
2. B.C. Cunningham, and J.A. Wells Science 244 1989 1081 1085
3. A.A. Bogan, and K.S. Thorn J. Mol. Biol. 280 1998 1 9
4. Peptidic scaffolds including those based on alpha amino acids: D.H. Appella, L.A. Christianson, I.L. Karle, D.R. Powell, and S.H. Gellman J. Am. Chem. Soc. 118 1996 13071 13072
5. J.A. Kritzer, O.M. Stephens, D.A. Guarracino, S.K. Reznik, and A. Schepartz Bioorg. Med. Chem. 13 2005 11 16
6. C.E. Schafmeister, J. Po, and G.L. Verdine J. Am. Chem. Soc. 122 2000 5891 5892
7. A. Patgiri, A.L. Jochim, and P.S. Arora Acc. Chem. Res. 41 2008 1289 1300
8. J. Liu, D. Wang, Q. Zheng, M. Lu, and P.S. Arora J. Am. Chem. Soc. 130 2008 4334 4337
9. M. Scrima, A. Le Chevalier-Isaad, P. Rovero, A.M. Papini, M. Chorev, and A.M. D'Ursi Eur. J. Org. Chem. 2010 2010 446 457
10. E. Ko, J. Liu, L.M. Perez, G.L. Lu, A. Schaefer, and K. Burgess J. Am. Chem. Soc. 133 2011 462 477
11. M.J. Adler, A.G. Jamieson, and A.D. Hamilton Small-Molecule Inhibitors of Protein-Protein Interactions 2011 Springer Berlin
12. J.A. Wells, and C.L. McClendon Nature 450 2007 1001 1009
13. S. Fletcher, and A.D. Hamilton Curr. Top. Med. Chem. 7 2007 922 927
14. J.M. Davis, L.K. Tsou, and A.D. Hamilton Chem. Soc. Rev. 36 2007 326 334
15. S. Fletcher, and A.D. Hamilton J.R. Soc. Interface 3 2006 215 233
16. M.J. Adler, and A.D. Hamilton J. Org. Chem. 76 2011 7040 7047
17. J.M. Rodriguez, and A.D. Hamilton Tetrahedron Lett. 47 2006 7443 7446
18. S. Marimganti, M.N. Cheemala, and J.-M. Ahn Org. Lett. 11 2009 4418 4421
19. J. Becerril, and A.D. Hamilton Angew. Chem., Int. Ed. 46 2007 4471 4473
20. I.C. Kim, and A.D. Hamilton Org. Lett. 8 2006 1751 1754
21. S. Hirano, M. Kawasaki, H. Ura, R. Kato, C. Raiborg, H. Stenmark, and S. Wakatsuki Nat. Struct. Mol. Biol. 13 2006 272 277
22. I. Huber, M. Rotman, E. Pick, V. Makler, L. Rothem, E. Cukierman, and D. Cassel Methods Enzymol. 329 2001 307 316
23. S. Runge, H. Thogersen, K. Madsen, J. Lau, and R. Rudolph J. Biol. Chem. 283 2008 11,340 11,347
24. R.E.W. Hancock, and A. Rozek FEMS Microbiol. Lett. 206 2002 143 149
25. I. Saraogi, J.A. Hebda, J. Becerril, L.A. Estroff, A.D. Miranker, and A.D. Hamilton Angew. Chem., Int. Ed. 49 2010 736 739
26. I. Saraogi, C.D. Incarvito, and A.D. Hamilton Angew. Chem., Int. Ed. 47 2008 9691 9694
27. J.-M. Ahn, and S.Y. Han Tetrahedron Lett. 48 2007 3543 3547
28. CCDC #s
29. compound 10: 850703
30. compound 12: 850704.
31. Calculated for the terminal carbon atoms corresponding to the i, i+2, i+4, i+6 residues using Chimera University of California, San Francisco (supported by NIH P41 RR001081): C.C. Huang, G.S. Couch, E.F. Pettersen, and T.E. Ferrin Pacific Symposium on Biocomputing Vol. 1 1996 724
32. A. Iyobe, M. Uchida, K. Kamata, Y. Hotei, H. Kusama, and H. Harada Chem. Pharm. Bull. 49 2001 822 829
33. A. Wissner, E. Overbeek, M.F. Reich, M.B. Floyd, B.D. Johnson, N. Mamuya, E.C. Rosfjord, C. Discafani, R. Davis, X. Shi, S.K. Rabindran, B.C. Gruber, F. Ye, W.A. Hallett, R. Nilakantan, R. Shen, Y.-F. Wang, L.M. Greenberger, and H.-R. Tsou J. Med. Chem. 46 2003 49 63
34. J.C.S. Dewar J. Chem. Soc. 1944 618 623