The Use of a Combination of RDC and Chiroptical Spectroscopy for Determination of the Absolute Configuration of Fusariumin A from the Fungus Fusarium sp

doi:10.1007/s13659-015-0084-0

Natural Products and Bioprospecting ›› 2016, Vol. 6 ›› Issue (1): 41-48.DOI: 10.1007/s13659-015-0084-0

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The Use of a Combination of RDC and Chiroptical Spectroscopy for Determination of the Absolute Configuration of Fusariumin A from the Fungus Fusarium sp

Liang-Yan Liu¹, Han Sun^2,3, Christian Griesinger², Ji-Kai Liu⁴

1. College of Agronomy and Biotechnology, Yunnan Agricultural University, Kunming 650201, China;
2. Department of NMR-based Structural Biology, Max-PlanckInstitute of Biophysical Chemistry, Am Fassberg 11, 37077 G?ttingen, Germany;
3. Leibniz-Institut für Molekulare Pharmakologie, 13125 Berlin, Germany;
4. School of Pharmaceutical Sciences, South-Central University for Nationalities, Wuhan 430074, China

Received:2015-10-11 Revised:2015-12-21 Online:2018-02-08 Published:2016-02-24
Supported by:
Support by the National Natural Science Foundation of China (U1132607) to J.K.L.and the DFG (Forschergruppe FOR 934) to C.G.as well as the Chinese/German foundation (GZ1104) to H.S.and C.G.is acknowledged

The Use of a Combination of RDC and Chiroptical Spectroscopy for Determination of the Absolute Configuration of Fusariumin A from the Fungus Fusarium sp

Liang-Yan Liu¹, Han Sun^2,3, Christian Griesinger², Ji-Kai Liu⁴

1. College of Agronomy and Biotechnology, Yunnan Agricultural University, Kunming 650201, China;
2. Department of NMR-based Structural Biology, Max-PlanckInstitute of Biophysical Chemistry, Am Fassberg 11, 37077 G?ttingen, Germany;
3. Leibniz-Institut für Molekulare Pharmakologie, 13125 Berlin, Germany;
4. School of Pharmaceutical Sciences, South-Central University for Nationalities, Wuhan 430074, China

通讯作者: Christian Griesinger,e-mail:cigr@nmr.mpibpc.mpg.de;Ji-Kai Liu,e-mail:jkliu@mail.kib.ac.cn
基金资助:
Support by the National Natural Science Foundation of China (U1132607) to J.K.L.and the DFG (Forschergruppe FOR 934) to C.G.as well as the Chinese/German foundation (GZ1104) to H.S.and C.G.is acknowledged

Abstract

Abstract: A new alkylpyrrole derivative, fusariumin A (1), was isolated from the culture broth of the fungus Fusarium sp. The absolute configuration of fuasiumin A has been established as (2'R,3'R) using a combination of RDC (residual dipolar coupling)-based NMR and DFT-supported chiroptical spectroscopy. It is worth to note that in this study without the aid of the RDC analysis, an unambiguous determination of configuration and conformation was not feasible due to the excessive conformational possibilities of this open-chain compound.

Key words: NMR, Residual dipolar coupling, Relative configuration, Absolute configuration, Chiroptics

摘要： A new alkylpyrrole derivative, fusariumin A (1), was isolated from the culture broth of the fungus Fusarium sp. The absolute configuration of fuasiumin A has been established as (2'R,3'R) using a combination of RDC (residual dipolar coupling)-based NMR and DFT-supported chiroptical spectroscopy. It is worth to note that in this study without the aid of the RDC analysis, an unambiguous determination of configuration and conformation was not feasible due to the excessive conformational possibilities of this open-chain compound.

关键词: NMR, Residual dipolar coupling, Relative configuration, Absolute configuration, Chiroptics

Liang-Yan Liu, Han Sun, Christian Griesinger, Ji-Kai Liu. The Use of a Combination of RDC and Chiroptical Spectroscopy for Determination of the Absolute Configuration of Fusariumin A from the Fungus Fusarium sp[J]. Natural Products and Bioprospecting, 2016, 6(1): 41-48.

References

1. C.M. Placinat, J.P.F. D'Mello, A.M.C. Macdonald, Anim. Feed Sci. Technol. 78, 21-37 (1999)
2. Q.H. Wu, V. Dohnal, K. Kuča, Z.H. Yuan, Curr. Drug Metab. 14, 641-660 (2013)
3. S.P. McCormick, A.M. Stanley, N.A. Stover, N.J. Alexander, Toxins 3, 802-814 (2011)
4. A.E. Desjardins, R.H. Proctor, Int. J. Food Microbiol. 119, 47-50 (2007)
5. C.M. Maragos, M. Busman, R.D. Plattner, Food Addit. Contam. 25, 105-114 (2008)
6. K. Kleigrewe, F. Aydin, K. Hogrefe, P. Piecuch, K. Bergander, E.U. Würthwein, H.U. Humpf, J. Agric. Food Chem. 60, 5497-5505 (2012)
7. C. Dall'Asta, C. Falavigna, G. Galaverna, P. Battilani, J. Agric. Food Chem. 60, 3800-3808 (2012)
8. S.J. Duncan, S.G. Dudley, H. Williams, C. McNicholas, R. Purewal, M. Hajek, M. Gerlitz, S. Martin, S.K. Wrigley, M. Moore, J. Am. Chem. Soc. 123, 554-560 (2001)
9. C. Aroulanda, V. Boucard, F. Guibe, J. Courtieu, D. Merlet, Chem. Eur. J. 9, 4536-4539 (2003)
10. C.M. Thiele, A. Marx, R. Berger, J. Fischer, M. Biel, A. Giannis, Angew. Chem. Int. Ed. 45, 4455-4460 (2006)
11. A. Schuetz, J. Junker, A. Leonov, O.F. Lange, T.F. Molinski, C. Griesinger, J. Am. Chem. Soc. 129, 15114-15115 (2007)
12. M.E. Garcia, S. Pagola, A. Navarro-Vazquez, D.D. Phillips, C. Gayathri, H. Krakauer, P.W. Stephens, V.E. Nicotra, R.R. Gil, Angew. Chem. Int. Ed. 45, 4455-4460 (2009)
13. G. Kummerlowe, B. Luy, TrAC Trend. Anal. Chem. 28, 483-493 (2009)
14. H. Sun, U.M. Reinscheid, E.L. Whitson, E.J. d'Auvergne, C.M. Ireland, J. Am. Chem. Soc. 133, 14629-14636 (2011)
15. V. Schmids, M. Fredersdorf, T. Lübken, A. Porzel, N. Arnold, L. Wessjohann, C.M. Thiele, J. Nat. Prod. 76, 839-844 (2013)
16. U.M. Reinscheid, M. Koeck, C. Cychon, V. Schmidts, C.M. Thiele, C. Griesinger, Eur. J. Org. Chem. 2010, 6900-6903 (2010)
17. H. Sun, E.J. d'Auvergne, U.M. Reinscheid, L.C. Dias, C.K. Andrade, R.O. Rocha, C. Griesinger, Chem. Eur. J. 17, 1811-1817 (2011)
18. M. Schmidt, H. Sun, P. Rogne, G.K. Scriba, C. Griesinger, L.T. Kuhn, U.M. Reinscheid, J. Am. Chem. Soc. 134, 3080-3083 (2012)
19. P. Trigo-Mourino, R. Sifuentes, A. Navarro-Vazquez, C. Gayathri, H. Maruenda, R.R. Gil, Nat. Prod. Commun. 7, 735-738 (2012)
20. D. Nasipuri, Stereochemistry of organic compounds:principles and applications, 4th revised ed. edn. (New Academic Science, London, 2012)
21. H.M. Ge, H. Sun, N. Jiang, Y.H. Qin, H. Dou, T. Yan, Y.Y. Hou, C. Griesinger, R.X. Tan, Chem. Eur. J. 18, 5213-5221 (2012)
22. J.A. Losonczi, M. Andrec, M.W. Fischer, J.H. Prestegard, J. Magn. Reson. 138, 334-342 (1999)
23. G. Cornilescu, J. Marquardt, M. Ottiger, A. Bax, J. Am. Chem. Soc. 120, 6836-6837 (1998)
24. N. Cyr, G.K. Hamer, A.S. Perlin, Can. J. Chem. 56, 297-301 (1978)
25. R. Riccio, G. Bifulco, P. Cimino, C. Bassarello, L. GomezPaloma, Pure Appl. Chem. 75, 295-308 (2003)
26. V.M. Sanchez-Pedregal, R. Santamaría-Fernandez, A. NavarroVazquez, Org. Lett. 11, 1471-1474 (2009)
27. C. Pérez-Balado, H. Sun, C. Griesinger, A.R. de Lera, A. Navarro-Vazquez, Chem. Eur. J. 17, 11983-11986 (2011)
28. M.D. Wodrich, C. Corminboeuf, P.R. Schreiner, A.A. Fokin, P. von RaguéSchleyer, Org. Lett. 9, 1851-1854 (2007)
29. C. Diedrich, S. Grimme, J. Phys. Chem. A 107, 2524-2539 (2003)
30. R. Hoffmann, Angew. Chem. Int. Ed. 39, 2054-2070 (2000)
31. A. Enthart, J.C. Freudenberger, J. Furrer, H. Kessler, B. Luy, J. Magn. Reson. 192, 314-322 (2008)
32. W. Kozminski, D. Nanz, J. Magn. Reson. 124, 383-392 (1997)
33. R.T. Williamson, B.L. Marquez, W.H. Gerwick, K.E. Kovér, Magn. Reson. Chem. 38, 265-273 (2000)
34. M.J. Thrippleton, J. Keeler, Angew. Chem. Int. Ed. 42, 3938-3941 (2003)
35. S. Lifson, A. Warshel, J. Chem. Phys. 49, 5116-5129 (1968)
36. M.J. Frisch, G.W. Trucks, H.B. Schlegel, J.V. Ortiz, J. Cioslowski, D.J. Fox, Gaussian 09 revision A.1 (Gaussian Inc., Wallingford, 2009)
37. A. Navarro-Vazquez, Magn. Reson. Chem. 50(S1), S73-S79 (2012)

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The Use of a Combination of RDC and Chiroptical Spectroscopy for Determination of the Absolute Configuration of Fusariumin A from the Fungus Fusarium sp

The Use of a Combination of RDC and Chiroptical Spectroscopy for Determination of the Absolute Configuration of Fusariumin A from the Fungus Fusarium sp

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