Intimate interactions with carbonyl groups: Dipole-dipole or n →π*?

Journal of Organic Chemistry

Volumn 78, Issue 5, 2013, Pages 2099-2103

  Kamer, Kimberli J ^a   Choudhary, Amit ^a,b   Raines, Ronald T ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

^b HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDES; VAN DER WAALS FORCES;

CARBONYL GROUPS; DIPOLE-DIPOLE; VAN DER WAALS RADIUS;

DIHEDRAL ANGLE;

CARBONYL DERIVATIVE; HALOGEN;

ARTICLE; CHEMICAL INTERACTION; CRYSTAL STRUCTURE; DIPOLE; PROTEIN SECONDARY STRUCTURE; PROTEIN STRUCTURE;

EID: 84874582783     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo302265k     Document Type: Article

References (57)

1. Bartlett, G. A.; Choudhary, A.; Raines, R. T.; Woolfson, D. N. Nat. Chem. Biol. 2010, 6, 615-620
2. Olsen, J. A.; Banner, D. W.; Seiler, P.; Obst Sander, U.; D'Arcy, A.; Stihle, M.; Müller, K.; Diederich, F. Angew. Chem., Int. Ed. 2003, 42, 2507-2511
3. Olsen, J. A.; Banner, D. W.; Seiler, P.; Wagner, B.; Tschopp, T.; Obst-Sander, U.; Kansy, M.; Müller, K.; Diederich, F. ChemBioChem 2004, 5, 666-675
4. Hof, F.; Scofield, D. M.; Schweizer, W. B.; Diederich, F. Angew. Chem., Int. Ed. 2004, 43, 5056-5059
5. Paulini, R.; Müller, K.; Diederich, F. Angew. Chem., Int. Ed. 2005, 44, 1788-1805
6. Fischer, F. R.; Schweizer, W. B.; Diederich, F. Angew. Chem., Int. Ed. 2007, 46, 8270-8273
7. Bissantz, C.; Kuhn, B.; Stahl, M. J. Med. Chem. 2010, 53, 5061-5084
8. Adler, M.; Davey, D. D.; Phillips, G. B.; Kim, S. H.; Jancarik, J.; Rumennik, G.; Light, D. R.; Whitlow, M. Biochemistry 2000, 39, 12534-12542
9. Horton, J. R.; Sawada, K.; Nishibori, M.; Zhang, X.; Cheng, X. Structure 2001, 9, 837-849
10. Perczel, A.; Angyan, J. G.; Kajtar, M.; Viviani, W.; Rivail, J. L.; Marcoccia, J. F.; Csizmadia, I. G. J. Am. Chem. Soc. 1991, 113, 6256-6265
11. Yang, A.-S.; Honig, B. J. Mol. Biol. 1995, 252, 351-365
12. Cantor, C. R.; Schimmel, P. R. Biophysical Chemistry, Part III: The Behavior of Biological Macromolecules; Freeman and Company: New York, NY, 2004.
13. Lesarri, A.; Cocinero, E. J.; López, J. C.; Alonso, J. L. J. Am. Chem. Soc. 2005, 127, 2572-2579
14. Blanco, S.; López, J. C.; Mata, S.; Alonso, J. L. Angew. Chem., Int. Ed. 2010, 49, 9187-9192
15. Choudhary, A.; Kamer, K. J.; Raines, R. T. J. Org. Chem. 2011, 76, 7933-7937
16. Cabezas, C.; Alonso, J. L.; López, J. C.; Mata, S. Angew. Chem., Int. Ed. 2012, 51, 1375-1378
17. Bretscher, L. E.; Jenkins, C. L.; Taylor, K. M.; DeRider, M. L.; Raines, R. T. J. Am. Chem. Soc. 2001, 123, 777-778
18. DeRider, M. L.; Wilkens, S. J.; Waddell, M. J.; Bretscher, L. E.; Weinhold, F.; Raines, R. T.; Markley, J. L. J. Am. Chem. Soc. 2002, 124, 2497-2505
19. Hinderaker, M. P.; Raines, R. T. Protein Sci. 2003, 12, 1188-1194
20. Jenkins, C. L.; Lin, G.; Duo, J.; Rapolu, D.; Guzei, I. A.; Raines, R. T.; Krow, G. R. J. Org. Chem. 2004, 69, 8565-8573
21. Horng, J.-C.; Raines, R. T. Protein Sci. 2006, 15, 74-83
22. Hodges, J. A.; Raines, R. T. Org. Lett. 2006, 8, 4695-4697
23. Sonntag, L.-S.; Schweizer, S.; Ochsenfeld, C.; Wennemers, H. J. Am. Chem. Soc. 2006, 128, 14697-14703
24. Kümin, M.; Sonntag, L.-S.; Wennemers, H. J. Am. Chem. Soc. 2007, 129, 466-467
25. Shoulders, M. D.; Guzei, I. A.; Raines, R. T. Biopolymers 2008, 89, 443-454
26. Dai, N.; Wang, X. J.; Etzkorn, F. A. J. Am. Chem. Soc. 2008, 130, 5396-5397
27. Chiang, Y.-C.; Lin, Y.-J.; Horng, J.-C. Protein Sci. 2009, 18, 1967-1977
28. Choudhary, A.; Gandla, D.; Krow, G. R.; Raines, R. T. J. Am. Chem. Soc. 2009, 131, 7244-7246
29. Dai, N.; Etzkorn, F. A. J. Am. Chem. Soc. 2009, 131, 13728-13732
30. Kuemin, M.; Schweizer, S.; Ochsenfeld, C.; Wennemers, H. J. Am. Chem. Soc. 2009, 131, 15474-15482
31. Choudhary, A.; Fry, C. G.; Raines, R. T. ARKIVOC 2010, 8, 251-262
32. Kuemin, M.; Nagel, Y. A.; Schweizer, S.; Monnard, F. W.; Ochsenfeld, C.; Wennemers, H. Angew. Chem., Int. Ed. 2010, 49, 6324-6327
33. Jakobsche, C. E.; Choudhary, A.; Miller, S. J.; Raines, R. T. J. Am. Chem. Soc. 2010, 132, 6651-6653
34. Choudhary, A.; Pua, K. H.; Raines, R. T. Amino Acids 2011, 41, 181-186
35. Choudhary, A.; Raines, R. T. Protein Sci. 2011, 20, 1077-1081
36. Pollock, S. B.; Kent, S. B. H. Chem. Commun. 2011, 47, 2342-2344
37. Erdmann, R. S.; Wennemers, H. J. Am. Chem. Soc. 2012, 134, 17117-17124
38. Gorske, B. C.; Bastian, B. L.; Geske, G. D.; Blackwell, H. E. J. Am. Chem. Soc. 2007, 129, 8928-8929
39. Gorske, B. C.; Stringer, J. R.; Bastian, B. L.; Fowler, S. A.; Blackwell, H. E. J. Am. Chem. Soc. 2009, 131, 16555-16567
40. Caumes, C.; Roy, O.; Faure, S.; Taillefumier, C. J. Am. Chem. Soc. 2012, 134, 9553-9556
41. Gao, J.; Kelly, J. W. Protein Sci. 2008, 17, 1096-1101
42. Fufezan, C. Proteins 2010, 78, 2831-2838
43. Choudhary, A.; Kamer, K. J.; Raines, R. T. Protein Sci. 2012, 21, 171-177
44. Choudhary, A.; Kamer, K. J.; Powner, M. W.; Sutherland, J. D.; Raines, R. T. ACS Chem. Biol. 2010, 5, 655-657
45. Liu, P.; Yang, X.; Birman, V. B.; Houk, K. N. Org. Lett. 2012, 14, 3288-3291
46. Wang, H.; Kohler, P.; Overman, L. E.; Houk, K. N. J. Am. Chem. Soc. 2012, 134, 16054-16058
47. Bürgi, H. B.; Dunitz, J. D.; Shefter, E. Acta Crystallogr. 1974, B30, 1517-1527
48. Allen, F. H. Acta Crystallogr. 2002, B58, 380-388
49. Bruno, I. J.; Cole, J. C.; Edgington, P. R.; Kessler, M.; Macrae, C. F.; McCabe, P.; Pearson, J.; Taylor, R. Acta Crystallogr. 2002, B58, 389-397
50. Macrae, C. F.; Edgington, P. R.; McCabe, P.; Pidcock, E.; Shields, G. P.; Taylor, R.; Towler, M.; van de Streek, J. J. Appl. Crystallogr. 2006, 39, 453-457
51. Dauber, P.; Hagler, A. T. Acc. Chem. Res. 1980, 13, 105-112
52. Dickerson, R. E.; Goodsell, D. S.; Neidle, S. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 3579-3583
53. Steiner, T. Angew. Chem., Int. Ed. 2002, 48-76
54. Worley, B.; Richard, G.; Harbison, G. S.; Powers, R. PLoS ONE 2012, 7, e42075
55. Zimmerman, H. E. Abstracts of the 17th National Organic Symposium of the American Chemical Society, Bloomington, IN; American Chemical Society: Washington, DC, 1961; pp 31-41.
56. Zimmerman, H. E. In Advances in Photochemistry; Noyes, W. A.; Hammond, G. S.; Pitts, J. N., Eds.; John Wiley: New York, NY, 1963; Vol. 1, pp 183-208.
57. Zimmerman, H. E. Pure Appl. Chem. 2006, 78, 2193-2203