Exploring β-hydroxy γ-amino acids (statines) in the design of hybrid peptide foldamers

Organic Letters

Volumn 16, Issue 1, 2014, Pages 294-297

  Bandyopadhyay, Anupam ^a   Malik, Ankita ^a   Kumar, Mothukuri Ganesh ^a   Gopi, Hosahudya N ^a  

^a INDIAN INSTITUTE OF SCIENCE EDUCATION AND RESEARCH   (India)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; PEPTIDE; STATINE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; PROTEIN FOLDING; STEREOISOMERISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

AMINO ACIDS; CRYSTALLOGRAPHY, X-RAY; MODELS, MOLECULAR; MOLECULAR CONFORMATION; PEPTIDES; PROTEIN FOLDING; STEREOISOMERISM;

EID: 84891821059     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol403290h     Document Type: Article

References (38)

1. Umezawa, H.; Aoyagi, T.; Morishima, H.; Matsuzaki, M.; Hamada, M.; Takeuchi, T. J. Antibiot. 1970, 23, 259
2. Dunn, B. M. Chem. Rev. 2002, 102, 4431
3. Leung, D.; Abbenante, G.; Fairlie, D. P. J. Med. Chem. 2000, 43, 305
4. Binkert, C.; Frigerio, M.; Jones, A.; Meyer, S.; Pesenti, C.; Prade, L.; Viani, F.; Zanda, M. ChemBioChem 2006, 7, 181
5. Rich, D. H.; Sun, E. T. O.; Ulm, E. J. Med. Chem. 1980, 23, 27
6. Zaidi, N.; Burster, T.; Sommandas, V.; Herrmann, T.; Boehm, B. O.; Driessen, C.; Voelter, W.; Kalbacher, H. Biochem. Biophys. Res. Commun. 2007, 364, 243
7. Matuz, K.; Motyan, J.; Li, M.; Wlodawer, A.; Tozser, J. FEBS J. 2012, 279, 3276
8. Barazza, A.; Gotz, M.; Cadamuro, S. A.; Goettig, P.; Willem, M.; Steuber, H.; Kohler, T.; Jestel, A.; Reinemer, P.; Renner, C.; Bode, W.; Moroder, L. ChemBioChem 2007, 8, 2078
9. Gupta, D.; Yedidi, R. S.; Varghese, S.; Kovari, L. C.; Woster, P. M. J. Med. Chem. 2010, 53, 4234
10. Bailey, D.; Cooper, J. B.; Veerapandian, B.; Blundell, T. L.; Atrash, B.; Jones, D. M.; Szelke, M. Biochem. J. 1993, 289, 363
11. Jones, D. M.; Sueiras-Diaz, J.; Szelke, M.; Leckie, B. J.; Beattie, S. R.; Morton, J.; Neidle, S.; Kuroda, R. J. Pep. Res. 1997, 50, 109
12. Vera, M. D.; Joullie, M. M. Med. Res. Rev. 2002, 22, 102
13. Pettit, G. R.; Kamano, Y.; Herald, C. L.; Fujii, Y.; Kizu, H.; Boyd, M. R.; Boettner, F. E.; Doubek, D. L.; Schmidt, J. M.; Chapuis, J.-C. Tetrahedron 1993, 49, 9151
14. Aherne, G. W.; Hardcastle, A.; Valenti, M.; Bryant, A.; Rogers, P.; Pettit, G. R.; Srirangam, J. K.; Kelland, L. R. Cancer Chemother. Pharmacol. 1996, 38, 225
15. Stratmann, K.; Burgoyne, D. L.; Moore, R. E.; Patterson, G. M. L.; Smith, C. D. J. Org. Chem. 1994, 59, 7219
16. Vervoort, H.; Fenical, W.; de A. Epifanio, R. J. Org. Chem. 2000, 65, 782
17. Ordonez, M.; Cativiela, C. Tetrahedron: Asymmetry 2007, 18, 3
18. Hintermann, T.; Gademann, K.; Jaun, B.; Seebach, D. Helv. Chim. Acta 1998, 81, 893
19. Hanessian, S.; Luo, X.; Schaum, R.; Michnick, S. J. Am. Chem. Soc. 1998, 120, 8569
20. Basuroy, K.; Dinesh, B.; Madhusudana Reddy, M. B.; Chandrappa, S.; Raghothama, S.; Shamala, N.; Balaram, P. Org. Lett. 2013, 15, 4866
21. Bandyopadhyay, A.; Gopi, H. N. Org. Lett. 2012, 14, 2770
22. Basuroy, K.; Dinesh, B.; Shamala, N.; Balaram, P. Angew. Chem., Int. Ed. 2012, 51, 8736
23. Shin, Y. H.; Mortenson, D. E.; Satyshur, K. A.; Forest, K. T.; Gellman, S. H. J. Am. Chem. Soc. 2013, 135, 8149
24. Pendem, N.; Nelli, Y. R.; Douat, C.; Fischer, L.; Laguerre, M.; Ennifar, E.; Kauffman, B.; Guichard, G. Angew. Chem., Int. Ed. 2013, 52, 4147
25. Bouillere, F.; Thetiot-Laurent, S.; Kouklovsky, C.; Alezra, V. Amino Acids 2011, 41, 687
26. Sharma, G. V. M.; Jadhav, V. B.; Ramakrishna, K. V. S.; Jayaprakash, P.; Narsimulu, K.; Subash, V.; Kunwar, A. C. J. Am. Chem. Soc. 2006, 128, 14657
27. Vasudev, P. G.; Chatterjee, S.; Shamala, N.; Balaram, P. Chem. Rev. 2011, 111, 657
28. Vasudev, P. G.; Chatterjee, S.; Shamala, N.; Balaram, P. Acc. Chem. Res. 2009, 42, 1628
29. Guo, L.; Chi, Y.; Almeida, A. M.; Guzei, I. A.; Parker, B. K.; Gellman, S. H. J. Am. Chem. Soc. 2009, 131, 16018
30. Guo, L.; Zhang, W.; Reidenbach, A. G.; Giuliano, M. W.; Guzei, I. A.; Spencer, L. C.; Gellman, S. H. Angew. Chem., Int. Ed. 2011, 50, 5843
31. Guo, L.; Zhang, W.; Guzei, I. A.; Spencer, L. C.; Gellman, S. H. Org. Lett. 2012, 14, 2582
32. Seebach, D.; Brenner, M.; Rueping, M.; Jaun, B. Chem.-Eur. J. 2002, 8, 573
33. Hagihara, M.; Anthony, N. J.; Stout, T. J.; Clardy, J.; Schreiber, S. L. J. Am. Chem. Soc. 1992, 114, 6568
34. Bandyopadhyay, A.; Mali, S. M.; Lunawat, P.; Raja, K. M. P.; Gopi, H. N. Org. Lett. 2011, 13, 4482
35. Jadhav, S. V.; Gopi, H. N. Chem. Commun. 2013, 49, 9179
36. Bandyopadhyay, A.; Agarwal, N.; Mali, S. M.; Jadhav, S. V.; Gopi, H. N. Org. Biomol. Chem. 2010, 8, 4855
37. Holmquist, C. R.; Roskamp, E. J. J. Org. Chem. 1989, 54, 3258
38. Maibaum, J.; Rich, D. H. J. Org. Chem. 1988, 53, 869