New preorganized γ-amino acids as foldamer building blocks

Organic Letters

Volumn 14, Issue 10, 2012, Pages 2582-2585

  Guo, Li ^a,b   Zhang, Weicheng ^a   Guzei, Ilia A ^a   Spencer, Lara C ^a   Gellman, Samuel H ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

^b DOW CHEMICAL COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; CYCLOHEXENE; CYCLOHEXENE DERIVATIVE; PEPTIDE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; HYDROGEN BOND; PROTEIN SECONDARY STRUCTURE; STEREOISOMERISM; SYNTHESIS;

AMINO ACIDS; CYCLOHEXENES; HYDROGEN BONDING; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; PEPTIDES; PROTEIN STRUCTURE, SECONDARY; STEREOISOMERISM;

EID: 84862091118     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol3008815     Document Type: Article

References (39)

1. Guichard, G.; Huc, I. Chem. Commun. 2011, 47, 5933
2. Hecht, S.; Huc, I., Eds. Foldamers: Structure, Properties and Applications; Wiley-VCH: Weinheim, Germany, 2007.
3. Seebach, D.; Beck, A. K.; Bierbaum, D. J. Chem. Biodiversity 2004, 1, 1111
4. Hanessian, S.; Luo, X.; Schaum, R.; Michnick, S. J. Am. Chem. Soc. 1998, 120, 8569
5. Hintermann, T.; Gademann, K.; Jaun, B.; Seebach, D. Helv. Chim. Acta 1998, 81, 983
6. Seebach, D.; Brenner, M.; Rueping, M.; Schweizer, B.; Jaun, B. Chem. Commun. 2001, 207
7. Baldauf, C.; Gunther, R.; Hofmann, H. J. Helv. Chim. Acta 2003, 86, 2573
8. Farrera-Sinfreu, J.; Zaccaro, L.; Vidal, D.; Salvatella, X.; Giralt, E.; Pons, M.; Albericio, F.; Royo, M. A. J. Am. Chem. Soc. 2004, 126, 6048
9. Claudon, P.; Violette, A.; Lamour, K.; Decossas, M.; Fournel, S.; Heurtault, B.; Godet, J.; Mely, Y.; Jamart-Gregoire, B.; Averlant-Petit, M.-C.; Briand, J.-P.; Duportail, G.; Monteil, H.; Guichard, G. Angew. Chem., Int. Ed. 2010, 49, 333
10. Hagihara, M.; Anthony, N. J.; Stout, T. J.; Clardy, J.; Schreiber, S. L. J. Am. Chem. Soc. 1992, 114, 6568
11. Karle, I. L.; Pramanik, A.; Banerjee, A.; Bhattacharjya, S.; Balaram, P. J. Am. Chem. Soc. 1997, 119, 9087
12. Ananda, K.; Vasudev, P. G.; Sengupta, A.; Raja, K. M. P.; Shamala, N.; Balaram, P. J. Am. Chem. Soc. 2005, 127, 16668
13. Qureshi, M. K. N.; Smith, M. Chem. Commun. 2006, 5006
14. Baldauf, C.; Gunther, R.; Hofmann, H. J. J. Org. Chem. 2006, 71, 1200
15. Sharma, G. V. M.; Jadhav, V. B.; Ramakrishna, K. V. S.; Narsimulu, K.; Subash, V.; Kunwar, A. C. J. Am. Chem. Soc. 2006, 128, 14657
16. Baruah, P. K.; Sreedevi, N. K.; Gonnade, R.; Ravindranathan, S.; Damodaran, K.; Hofmann, H. J.; Sanjayan, G. J. J. Org. Chem. 2007, 72, 636
17. Vasudev, P. G.; Ananda, K.; Chatterjee, S.; Aravinda, S.; Shamala, N.; Balaram, P. J. Am. Chem. Soc. 2007, 129, 4039
18. Chatterjee, S.; Vasudev, P. G.; Raghothama, S.; Ramakrishnan, C.; Shamala, N.; Balaram, P. J. Am. Chem. Soc. 2009, 131, 5956
19. Araghi, R. R.; Jäckel, C.; Cölfen, H.; Salwiczek, M.; Vokel, A.; Wagner, S. C.; Wieczorek, S.; Baldauf, C.; Koksch, B. ChemBioChem 2010, 11, 335
20. Araghi, R. R.; Baldauf, C.; Gerling, U. I. M.; Cadicamo, C. D.; Koksch, B. Amino Acids 2011, 41, 733
21. Raguse, T. L.; Lai, J. R.; Gellman, S. H. J. Am. Chem. Soc. 2003, 125, 5592
22. Schmitt, M. A.; Choi, S. H.; Guzei, I. A.; Gellman, S. H. J. Am. Chem. Soc. 2005, 127, 13130
23. Horne, W. S.; Gellman, S. H. Acc. Chem. Res. 2008, 41, 1399
24. Horne, W. S.; Johnson, L. M.; Ketas, T. J.; Klasse, P. J.; Lu, M.; Moore, J. P.; Gellman, S. H. Proc. Natl. Acad. Sci. U.S.A. 2009, 106, 14751
25. Price, J. L.; Hadley, E. B.; Steinkruger, J. D.; Gellman, S. H. Angew. Chem., Int. Ed. 2010, 49, 368
26. Woll, M. G.; Lai, J. R.; Guzei, I. A.; Taylor, S. J. C.; Smith, M. E. B.; Gellman, S. H. J. Am. Chem. Soc. 2001, 123, 11077
27. Qureshi, M. K. N.; Smith, M. Chem. Commun. 2006, 5006
28. Guo, L.; Chi, Y.; Almeida, A. M.; Guzei, I. A.; Parker, B. K.; Gellman, S. H. J. Am. Chem. Soc. 2009, 131, 16018
29. Guo, L.; Almeida, A. M.; Zhang, W.; Reidenbach, A. G.; Choi, S. H.; Guzei, I. A.; Gellman, S. H. J. Am. Chem. Soc. 2010, 132, 7868
30. Sawada, T.; Gellman, S. H. J. Am. Chem. Soc. 2011, 133, 7336
31. Guo, L.; Zhang, W.; Reidenbach, A. G.; Giuliano, J. W.; Guzei, I. A.; Spencer, L. C.; Gellman, S. H. Angew. Chem., Int. Ed. 2011, 50, 5843
32. For an altertnative synthesis of γ amino acids of type I, see: Nodes, W. J.; Nutt, D. R.; Chippindale, A. M.; Cobb, A. J. A. J. Am. Chem. Soc. 2009, 131, 16016
33. For racemic synthesis of γ-amino acids corresponding to residues II and III, see: Johnson, M. R.; Gauuan, J. F.; Guo, C.; Guzzo, P. R.; Le, V.-D.; Shenoy, R. A.; Hamby, J.; Roark, H.; Stier, M.; Mangette, J. E. Synth. Commun. 2011, 41, 2769
34. For asymmetric synthesis of the cyclobutane analogue of 3c, see: André, V.; Vidal, A.; Ollivier, J.; Robin, S.; Aitken, D. J. Tetrahedron Lett. 2011, 52, 1253
35. Gotoh, H.; Ishikawa, H.; Hayashi, Y. Org. Lett. 2007, 9, 5307
36. Zu, L.; Xie, H.; Li, H.; Wang, J.; Wang, W. Adv. Synth. Catal. 2007, 349, 2660
37. Barlow, D. J; Thorton, J. M. J. Mol. Biol. 1988, 5, 601
38. Sugeta, H.; Miyazawa, T. Biopolymers 1967, 5, 673
39. Kahn, P. C. Comput. Chem. 1989, 13, 185