Constitutional, configurational, and conformational analysis of small organic molecules on the basis of NMR residual dipolar couplings

Angewandte Chemie - International Edition

Volumn 50, Issue 32, 2011, Pages 7222-7224

  Gil, Roberto R ^a  

^a CARNEGIE MELLON UNIVERSITY   (United States)

Author keywords

configuration determination; conformation analysis; NMR spectroscopy; residual dipolar couplings; structure elucidation

Indexed keywords

CHEMICAL CONSTITUTION; CONFIGURATION DETERMINATION; CONFORMATION ANALYSIS; CONFORMATIONAL ANALYSIS; RESIDUAL DIPOLAR COUPLINGS; SMALL ORGANIC MOLECULES; SPECTROSCOPIC TECHNIQUE; STRUCTURE ELUCIDATION; SYNTHETIC ORGANIC COMPOUNDS;

COUPLINGS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORGANIC COMPOUNDS; ORGANIC SOLVENTS; SPECTROSCOPIC ANALYSIS;

CONFORMATIONS;

EID: 79960897661     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201101561     Document Type: Article

References (43)

1. F. A. L. Anet, A. J. R. Bourn, J. Am. Chem. Soc. 1965, 87, 5250.
2. M. Karplus, J. Chem. Phys. 1959, 30, 11
3. C. A. G. Haasnoot, F. Deleeuw, C. Altona, Tetrahedron 1980, 36, 2783.
4. For selected articles and reviews on residual dipolar couplings, see
5. A. Bax, G. Kontaxis, N. Tjandra, Methods Enzymol. 2001, 339, 127
6. J. H. Prestegard, C. M. Bougault, A. I. Kishore, Chem. Rev. 2004, 104, 3519
7. F. Kramer, M. V. Deshmukh, H. Kessler, S. J. Glaser, Concepts Magn. Reson. Part A 2004, 21A, 10
8. M. Blackledge, Prog. Nucl. Magn. Reson. Spectrosc. 2005, 46, 23
9. C. M. Thiele, Concepts Magn. Reson. Part A 2007, 30A, 65
10. C. M. Thiele, Eur. J. Org. Chem. 2008, 5673
11. G. Kummerlöwe, B. Luy, TrAC Trends Anal. Chem. 2009, 28, 483
12. "Residual Dipolar Couplings for the Configurational, and, Conformational Analysis of Organic Molecules": G. Kummerlöwe, B. Luy, A. W. Graham, Annual Reports on NMR Spectroscopy, Vol. 68, Elsevier Academic Press Inc., San Diego, 2009, p. 193.
13. A. Saupe, G. Englert, Phys. Rev. Lett. 1963, 11, 462.
14. N. Tjandra, A. Bax, Science 1997, 278, 1111
15. J. R. Tolman, H. M. Al-Hashimi, L. E. Kay, J. H. Prestegard, J. Am. Chem. Soc. 2001, 123, 1416
16. W. Peti, J. Meiler, R. Bruschweiler, C. Griesinger, J. Am. Chem. Soc. 2002, 124, 5822
17. A. Bax, A. Grishaev, Curr. Opin. Struct. Biol. 2005, 15, 563.
18. A. Mangoni, V. Esposito, A. Randazzo, Chem. Commun. 2003, 154.
19. J. L. Yan, A. D. Kline, H. P. Mo, M. J. Shapiro, E. R. Zartler, J. Org. Chem. 2003, 68, 1786.
20. C. Aroulanda, V. Boucard, F. Guibe, J. Courtieu, D. Merlet, Chem. Eur. J. 2003, 9, 4536
21. C. M. Thiele, S. Berger, Org. Lett. 2003, 5, 705
22. L. Verdier, P. Sakhaii, M. Zweckstetter, C. Griesinger, J. Magn. Reson. 2003, 163, 353.
23. B. Luy, K. Kobzar, H. Kessler, Angew. Chem. 2004, 116, 1112
24. Angew. Chem. Int. Ed. 2004, 43, 1092.
25. G. Kummerlöwe, E. F. McCord, S. F. Cheatham, S. Niss, R. W. Schnell, B. Luy, Chem. Eur. J. 2010, 16, 7087.
26. C. Gayathri, N. V. Tsarevsky, R. R. Gil, Chem. Eur. J. 2010, 16, 3622.
27. For selected examples of the configurational and/or conformational analysis of small molecules on the basis of RDCs, see
28. C. M. Thiele, J. Org. Chem. 2004, 69, 7403
29. M. E. García, S. Pagola, A. Navarro-Vázquez, D. D. Phillips, C. Gayathri, H. Krakauer, P. W. Stephens, V. E. Nicotra, R. R. Gil, Angew. Chem. 2009, 121, 5780
30. Angew. Chem. Int. Ed. 2009, 48, 5670
31. A. Schuetz, J. Junker, A. Leonov, O. F. Lange, T. F. Molinski, C. Griesinger, J. Am. Chem. Soc. 2007, 129, 15114
32. A. Schuetz, T. Murakami, N. Takada, J. Junker, M. Hashimoto, C. Griesinger, Angew. Chem. 2008, 120, 2062
33. Angew. Chem. Int. Ed. 2008, 47, 2032
34. C. Gayathri, M. C. de la Fuente, B. Luy, R. R. Gil, A. Navarro-Vázquez, Chem. Commun. 2010, 46, 5879
35. J. Klages, C. Neubauer, M. Coles, H. Kessler, B. Luy, ChemBioChem 2005, 6, 1672
36. R. R. Gil, C. Gayathri, N. V. Tsarevsky, K. Matyjaszewski, J. Org. Chem. 2008, 73, 840
37. C. J. Arnusch, J. H. Ippel, H. Kooijman, A. L. Spek, R. M. J. Liskamp, J. Kemmink, R. J. Pieters, Eur. J. Org. Chem. 2010, 4501
38. C. Farès, J. Hassfeld, D. Menche, T. Carlomagno, Angew. Chem. 2008, 120, 3782
39. Angew. Chem. Int. Ed. 2008, 47, 3722
40. C. M. Thiele, A. Marx, R. Berger, J. Fischer, M. Biel, A. Giannis, Angew. Chem. 2006, 118, 4566
41. Angew. Chem. Int. Ed. 2006, 45, 4455.
42. G. Kummerlöwe, B. Crone, M. Kretschmer, S. F. Kirsch, B. Luy, Angew. Chem. 2011, 123, 2693
43. Angew. Chem. Int. Ed. 2011, 50, 2643.