Computing the NMR spectra of the sponge metabolite arsenicin A: When simple becomes difficult

Journal of Physical Organic Chemistry

Volumn 23, Issue 11, 2010, Pages 1016-1021

  Bagno, Alessandro ^a  

^a UNIVERSITY OF PADOVA   (Italy)

Author keywords

arsenic; computational chemistry; natural products; NMR spectroscopy; structure elucidation

Indexed keywords

NATURAL PRODUCTS; NMR SPECTROSCOPY; NMR SPECTRUM; STRUCTURE ELUCIDATION;

ARSENIC; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

COMPUTATIONAL CHEMISTRY;

EID: 78349292306     PISSN: 08943230     EISSN: 10991395     Source Type: Journal    
DOI: 10.1002/poc.1719     Document Type: Article

References (38)

1. This paper is a commentary from the lecture given at ESOR XII, Haifa, September 2009 and is based on the work of reference [29]; since the intended focus is to present the flow of events choronologically, there are some differences in presentation. (a) Putative structures are introduced in a different order; however, to avoid any confusion we have chosen to maintain the previous ordering and, as a consequence, putative structures do not appear in numerical order here. Also, structure 2 was incorrectly drawn in reference [29] and has been corrected here (we thank a Referee for pointing this out). (b) Keppler's compound, which is not an isomer of arsenicin A (2 in reference [29]) is named 13 here. (c) Computational details are only briefly listed below, as follows (see reference [29] for details). The structure of each species was optimized at the B3LYP/6-311G(2d,2p) level. NMR parameters were computed with several methods; the results reported in Figs 1 and 2 include shieldings calculated including relativistic corrections by means of the Zero-Order Regular Approximation (ZORA) up to spin-orbit coupling (ZSO) with the Becke88-Perdew86 GGA functional (BP) and a double-zeta, twice-polarized Slater basis set (TZ2P); coupling constants with the B3LYP functional and a mixed basis set comprising pcJ-2 for O, C, and H, and cc-pVTZ for As.
2. M. Kaupp, M. Bühl, V. G. Malkin, (Eds), Calculation of NMR and EPR Parameters, Wiley-VCH, Weinheim, 2004.
3. A. Bagno, M. Bonchio, Chem. Phys. Lett. 2000, 317, 123.
4. A. Bagno, G. Scorrano, Acc. Chem. Res. 2000, 33, 609.
5. A. Bagno, Chem. Eur. J. 2000, 6, 2925.
6. A. Bagno, G. Saielli, G. Scorrano, Angew. Chem. Int. Ed. 2001, 40, 2532
7. A. Bagno, G. Saielli, G. Scorrano, Chem. Eur. J. 2002, 8, 2047.
8. A. Bagno, Chem. Eur. J. 2001, 7, 1652.
9. A. Bagno, F. Rastrelli, G. Saielli, J. Phys. Chem. A 2003, 107, 9964.
10. A. Bagno, M. Bonchio, Eur. J. Inorg. Chem. 2002, 1475.
11. A. Bagno, M. Bonchio, A. Sartorel, G. Scorrano, ChemPhysChem 2003, 4, 517.
12. A. Bagno, G. Saielli, Chem. Eur. J. 2003, 9, 1486.
13. S. Berger, D. Sicker, Classics in Spectroscopy: Isolation and Structure Elucidation of Natural Products, Wiley-VCH, Weinheim, 2009.
14. K. C. Nicolaou, S. A. Snyder, Angew. Chem. Int. Ed. 2005, 44, 1012.
15. G. Saielli, A. Bagno, Org. Lett. 2009, 11, 1409.
16. I. Mancini, G. Guella, M. Frostin, E. Hnawia, D. Laurent, C. Debitus, F. Pietra, Chem. Eur. J. 2006, 12, 8989.
17. N. C. Lloyd, H. W. Morgan, B. K. Nicholson, R. S. Ronimus, Angew. Chem. Int. Ed. 2005, 44, 941.
18. S. V. Barrett, M. P. Barrett, Parasitol. Today 2000, 16, 7.
19. S. Waxman, K. C. Anderson, Oncologist 2001, 6, 3.
20. W. H. Miller, H. M. Schipper, J. S. Lee, J. Singer, S. Waxman, Cancer Res. 2002, 62, 3893.
21. H. Chen, R. C. MacDonald, S. Li, N. L. Krett, S. T. Rosen, T. V. O'Halloran, J. Am. Chem. Soc. 2006, 128, 13348.
22. J. Lu, E.-C. Chew, A. Holmgren, Proc. Natl. Acad. Sci. USA 2007, 104, 12288.
23. K. A. Francesconi, D. Kuehnelt, in Environmental Chemistry of Arsenic (Ed.:, W. T. Frankenberger,), Marcel Dekker, New York, 2002.
24. A. Kolozsi, A. Lakatos, G. Galbács, A. O. Madsen, E. Larsen, B. Gyurcsik, Inorg. Chem. 2008, 47, 3832 and references cited therein.
25. A. Bagno, F. Rastrelli, G. Saielli, Chem. Eur. J. 2006, 12, 5514.
26. K. R. Dixon, in Multinuclear NMR (Ed.:, J. Mason,), Plenum, New York, 1987.
27. M. E. Elyashberg, A. J. Williams, G. E. Martin, Prog. NMR Spectrosc. 2008, 53, 1.
28. M. Kaupp, O. L. Malkina, V. G. Malkin, P. Pyykkö, Chem. Eur. J. 1998, 4, 118.
29. P. Tähtinen, G. Saielli, G. Guella, I. Mancini, A. Bagno, Chem. Eur. J. 2008, 14, 10445.
30. A. Bagno, G. Saielli, Theor. Chem. Acc. 2007, 117, 603 - 619.
31. M. B. L. Marx, H. Pritzkow, B. K. Keppler, Z. Anorg. Allg. Chem. 1996, 622, 1097.
32. D. W. Rogers, O. P. A. Hoyte, R. K. C. Ho, J. Chem. Soc., Faraday Trans. 1 1978, 74, 46.
33. F. Jensen, J. Chem. Theory Comput. 2006, 2, 1360.
34. G. Guella, I. Mancini, G. Mariotto, B. Rossi, G. Viliani, Phys. Chem. Chem. Phys. 2009, 11, 2420.
35. D. Lu, A. D. Rae, G. Salem, M. L. Weir, A. C. Willis, S. B. Wild, Organometallics 2010, 29, 32.
36. A. J. Karttunen, M. Linnolahti, T. A. Pakkanen, ChemPhysChem 2007, 8, 2373.
37. P. Nava, R. Ahlrichs, Chem. Eur. J. 2008, 14, 4039.
38. P. Tähtinen, G. Guella, I. Mancini, A. Bagno, (in press).