Residual Dipolar Couplings in Structure Determination of Natural Products

doi:10.1007/s13659-018-0174-x

Natural Products and Bioprospecting

2018, Vol. 8

Issue (4) : 279-295 DOI: 10.1007/s13659-018-0174-x

REVIEWS

Residual Dipolar Couplings in Structure Determination of Natural Products

Gao-Wei Li², Han Liu¹, Feng Qiu¹, Xiao-Juan Wang², Xin-Xiang Lei¹

1 School of Pharmaceutical Sciences, South Central University for Nationalities, Wuhan 430074, People's Republic of China;
2 College of Chemistry and Chemical Engineering, Shangqiu Normal University, Shangqiu 476000, People's Republic of China

Abstract
References
Related Articles
Metrics

Download: PDF(7389 KB) HTML ()
Export: BibTeX | EndNote | Reference Manager | ProCite | RefWorks

Abstract The determination of natural products stereochemistry remains a formidable task. Residual dipolar couplings (RDCs) induced by anisotropic media are a powerful tool for determination of the stereochemistry of organic molecule in solution. This review will provide a short introduction on RDCs-based methodology for the structural elucidation of natural products. Special attention is given to the current availability of alignment media in organic solvents. The applications of RDCs for structural analysis of some examples of natural products were discussed and summarized.

Keywords NMR spectroscopy Residual dipolar couplings Alignment media Structural elucidation Natural products

Fund:The project was financially co-supported by National Natural Science Foundation of China (21572164, U1504207) and the Sino-German Center for Research Promotion (GZ1289).

Corresponding Authors: Xin-Xiang Lei,xxlei@mail.scuec.edu.cn E-mail: xxlei@mail.scuec.edu.cn

Issue Date: 28 August 2018

	Service

	E-mail this article
	E-mail Alert
	RSS
	Articles by authors

	Gao-Wei Li
	Han Liu
	Feng Qiu
	Xiao-Juan Wang
	Xin-Xiang Lei

Trendmd:

Cite this article:

Gao-Wei Li,Han Liu,Feng Qiu, et al. Residual Dipolar Couplings in Structure Determination of Natural Products[J]. Natural Products and Bioprospecting, 2018, 8(4): 279-295.

URL:

http://npb.kib.ac.cn/EN/10.1007/s13659-018-0174-x OR http://npb.kib.ac.cn/EN/Y2018/V8/I4/279

1. R.R. Gil, C. Griesinger, A. Navarro-Vázquez, H. Sun, Structure Elucidation in Organic Chemistry:The Search for the Right Tools, 1st edn. (Wiley-VCH, Weinheim, 2014), pp. 279-323
2. R.R. Gil, A. Navarro-Vázquez, Application of Residual Dipolar Couplings to the Structural Analysis of Natural Products, vol. 2 (The Royal Society of Chemistry, Cambridge, 2016), pp. 117-176
3. C.M. Thiele, Concepts Magn. Reson. Part A 30A, 65-80 (2007)
4. G. Kummerlöwe, B. Luy, Annu. Rep. NMR Spectrosc. 68, 193-232 (2009)
5. Jr J.M. Batista, E.W. Blanch, V. da Silva Bolzani, Nat. Prod. Rep. 32, 1280-1302 (2015)
6. B. Luy, H. Kessler, Partial Alignment for Structure Determination of Organic Molecules, chapt. 138 (Springer International Publishing, Modern Magnetic Resonance, 2006), pp. 1279-1285
7. C.M. Thiele, Eur. J. Org. Chem. 2008, 5673-5685 (2008)
8. A. Saupe, G. Englert, Phys. Rev. Lett. 11, 462-465 (1963)
9. B. Böttcher, C.M. Thiele, eMagRes 1, 169-180 (2012)
10. A. Canales, J. Jiménez-Barbero, M. Martín-Pastor, Magn. Reson. Chem. 50, S80-S85 (2012)
11. V. Schmidts, Magn. Reson. Chem. 55, 54-60 (2017)
12. P. Lesot, D. Merlet, A. Loewenstein, J. Courtieu. Tetrahedron:Asymmetry 9, 1871-1881 (1998)
13. P. Lesot, M. Sarfati, J. Courtieu, Chem. Eur. J. 9, 1724-1745 (2003)
14. P. Lesot, O. Lafon, C. Aroulanda, R.Y. Dong, Chem. Eur. J. 14, 4082-4092 (2008)
15. L. Arnold, A. Marx, C.M. Thiele, M. Reggelin, Chem. Eur. J. 16, 10342-10346 (2010)
16. N.C. Meyer, A. Krupp, V. Schmidts, C.M. Thiele, M. Reggelin, Angew. Chem. Int. Ed. 51, 8334-8338 (2012)
17. A. Krupp, M. Reggelin, Magn. Reson. Chem. 50, S45-S52 (2012)
18. M. Dama, S. Berger, Tetrahedron Lett. 53, 6439-6442 (2012)
19. M. Dama, S. Berge, Org. Lett. 14, 241-243 (2012)
20. M. Reller, S. Wesp, M.R.M. Koos, M. Reggelin, B. Luy, Chem. Eur. J. 23, 13351-13359 (2017)
21. G.W. Li, J.M. Cao, W. Zong, L. Hu, M.L. Hu, X. Lei, H. Sun, R.X. Tan, Chem. Eur. J. 23, 7653-7656 (2017)
22. X. Lei, F. Qiu, H. Sun, L. Bai, W.X. Wang, W. Xiang, H. Xiao, Angew. Chem. Int. Ed. 56, 12857-12861 (2017)
23. X. Lei, Z. Xu, H. Sun, S. Wang, C. Griesinger, L. Peng, C. Gao, R.X. Tan, J. Am. Chem. Soc. 136, 11280-11283 (2014)
24. W. Zong, G.W. Li, J.M. Cao, X. Lei, M.L. Hu, H. Sun, C. Griesinger, R.X. Tan, Angew. Chem. Int. Ed. 55, 3690-3693 (2016)
25. E. Troche-Pesqueira, M.M. Cid, A. Navarro-Vázquez, Org. Biomol. Chem. 12, 1957-1965 (2014)
26. C.M. Thiele, S. Berger, Org. Lett. 5, 705-708 (2003)
27. C. Aroulanda, M. Sarfati, J. Courtieu, Enantiomer. 6, 281-287 (2001)
28. C.M. Thiele, J. Org. Chem. 69, 7403-7413 (2004)
29. S. Hansmann, V. Schmidts, C.M. Thiele, Chem. Eur. J. 23, 9114-9121 (2017)
30. M. Schwab, D. Herold, C.M. Thiele, Chem. Eur. J. 23, 14576-14584 (2017)
31. C.M. Thiele, W.C. Pomerantz, N.L. Abbott, S.H. Gellman, Chem. Commun. 47, 502-504 (2011)
32. M. Leyendecker, N.C. Meyer, C.M. Thiele, Angew. Chem. Int. Ed. 56, 11471-11474 (2017)
33. V.V. Klochkov, A.V. Klochkov, C.M. Thiele, S. Berger, J. Magn. Reson. 179, 58-63 (2006)
34. M. Dama, S. Berger, Carbohyd. Res. 377, 44-47 (2013)
35. B. Luy, K. Kobzar, H. Kessler, Angew. Chem. Int. Ed. 43, 1092-1094 (2004)
36. G. Kummerlöwe, R. Knör, A.K. Frank, Chem. Commun. 44, 5722-5724 (2008)
37. J.C. Freudenberger, S. Knör, K. Kobzar, D. Heckmann, T. Paululat, H. Kessler, B. Luy, Angew. Chem. Int. Ed. 44, 423-426 (2005)
38. J.C. Freudenberger, P. Spiteller, B. Luy, J. Am. Chem. Soc. 126, 14690-14691 (2004)
39. Y.E. Moskalenko, V. Bagutski, C.M. Thiele, Chem. Commun. 53, 95-98 (2017)
40. R.R. Gil, C. Gayathri, N.V. Tsarevsky, K. Matyjaszewski, J. Org. Chem. 73, 840-848 (2008)
41. C. Merle, G. Kummerlöwe, J.C. Freudenberger, F. Halbach, W. Stöwer, C.L.V. Gostomski, J. Höpfner, T. Beskers, M. Wilhelm, B. Luy. Angew. Chem. Int. Ed. 52, 10309-10312 (2013)
42. K. Kobzar, H. Kessler, B. Luy, Angew. Chem. Int. Ed. 44, 3145-3147 (2005)
43. G. Kummerlöwe, M.U. Kiran, B. Luy, Chem. Eur. J. 15, 12192-12195 (2009)
44. J.H. Ma, G.I. Goldberg, N. Tjandra, J. Am. Chem. Soc. 130, 16148-16149 (2008)
45. T.S. Ulmer, B.E. Ramirez, F. Delaglio, A. Bax, J. Am. Chem. Soc. 125, 9179-9191 (2003)
46. P. Haberz, J. Farjon, C.A. Griesinger, Angew. Chem. Int. Ed. 44, 427-429 (2005)
47. M. Schmidt, H. Sun, A. Leonov, C. Griesinger, U.M. Reinscheid, Magn. Reson. Chem. 50, S38-S44 (2012)
48. G. Kummerlöwe, J. Auernheimer, A. Lendlein, B. Luy, J. Am. Chem. Soc. 129, 6080-6081 (2007)
49. T. Montag, C.M. Thiele, Chem. Eur. J. 19, 2271-2274 (2013)
50. L.F. Gil-Silva, R. Santamaría-Fernández, A. Navarro-Vázquez, R.R. Gil, Chem. Eur. J. 22, 472-476 (2016)
51. M.E. García, S.R. Woodruff, E. Hellemann, N.V. Tsarevsky, R.R. Gil, Magn. Reson. Chem. 55, 206-209 (2017)
52. R.C. Breton, W.F. Reynolds, Nat. Prod. Rep. 30, 501-524 (2013)
53. G. Bodenhausen, D.J. Ruben, Chem. Phys. Lett. 69, 185-189 (1980)
54. A. Enthart, J.C. Freudenberger, J. Furrer, H. Kessler, B. Luy, J. Magn. Reson. 192, 314-322 (2008)
55. K. Zangger, Prog. Nucl. Magn. Reson. Spectrosc. 86-87, 1-20 (2015)
56. L. Jin, T.N. Pham, D. Uhrín, ChemPhysChem 8, 1228-1235 (2007)
57. B. Yu, H. van Ingen, D.I. Freedberg, J. Magn. Reson. 228, 159-165 (2013)
58. H. Schwalbe, J.P. Marino, G.C. King, R. Wechselberger, W. Bermel, C. Griesinger, J. Biomol. NMR 5, 631-644 (1994)
59. A. Bax, R. Freeman, S.P. Kempsell, J. Am. Chem. Soc. 102, 4849-4851 (1980)
60. N. Nath, E.J. d'Auvergne, C. Griesinger, Angew. Chem. Int. Ed. 127, 12897-12901 (2015)
61. J.A. Losonczi, M. Andrec, M.W.F. Fischer, J.H. Prestegard, J. Magn. Reson. 138, 334-342 (1999)
62. A. Navarro-Vázquez, Magn. Reson. Chem. 50, S73-S79 (2012)
63. G. Cornilescu, J.L. Marquardt, M. Ottiger, A. Bax, J. Am. Chem. Soc. 120, 6836-6837 (1998)
64. C.M. Thiele, Angew. Chem. Int. Ed. 44, 2787-2790 (2005)
65. A. Mangoni, V. Esposito, A. Randazzo, Chem. Commun. 154-155 (2003)
66. J. Klages, C. Neubauer, M. Coles, H. Kessler, B. Luy, ChemBioChem 6, 1672-1678 (2005)
67. C.M. Thiele, A. Marx, R. Berger, J. Fischer, M. Biel, A. Giannis, Angew. Chem. Int. Ed. 45, 4455-4460 (2006)
68. C.M. Thiele, A. Maliniak, B. Stevensson, J. Am. Chem. Soc. 131, 12878-12879 (2009)
69. U.M. Reinscheid, J. Farjon, M. Radzom, P. Haberz, A. Zeeck, M. Blackledge, C. Griesinger, ChemBioChem 7, 287-296 (2006)
70. A. Schuetz, J. Junker, A. Leonov, O.F. Lange, T.F. Molinski, C. Griesinger, J. Am. Chem. Soc. 129, 15114-15115 (2007)
71. N. Cramer, S. Helbig, A. Baro, S. Laschat, R. Diestel, F. Sasse, D. Mathieu, C. Richter, G. Kummerlöwe, B. Luy, H. Schwalbe, ChemBioChem 9, 2474-2486 (2008)
72. C. Farès, J. Hassfeld, D. Menche, T. Carlomagno, Angew. Chem. Int. Ed. 47, 3722-3726 (2008)
73. A. Schuetz, T. Murakami, N. Takada, J. Junker, M. Hashimoto, C. Griesinger, Angew. Chem. Int. Ed. 47, 2032-2034 (2008)
74. 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. Int. Ed. 48, 5670-5674 (2009)
75. D. Intelmann, G. Kummerlöwe, G. Haseleu, N. Desmer, K. Schulze, R. Fröhlich, O. Frank, B. Luy, T. Hofmann, Chem. Eur. J. 15, 13047-13058 (2009)
76. N.V. Gayathri, K. Tsarevsky, R.R. Gil, Chem. Eur. J. 16, 3622-3626 (2010)
77. U.M. Reinscheid, M. Köck, C. Cychon, V. Schmidts, C.M. Thiele, C. Griesinger, Eur. J. Org. Chem. 2010, 6900-6903 (2010)
78. G. Kummerlöwe, E.F. McCord, S.F. Cheatham, S. Niss, R.W. Schnell, B. Luy, Chem. Eur. J. 16, 7087-7089 (2010)
79. H. Sun, U.M. Reinscheid, E.L. Whitson, E.J. d'Auvergne, C.M. Ireland, A. Navarro-Vázquez, C. Griesinger, J. Am. Chem. Soc. 133, 14629-14636 (2011)
80. C. Pérez-Balado, H. Sun, C. Griesinger, A.R. de Lera, A. Navarro-Vázquez, Chem. Eur. J. 17, 11983-11986 (2011)
81. 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)
82. P. Trigo-Mouriño, R. Sifuentes, A. Navarro-Vázquez, C. Gayathri, H. Maruenda, R.R. Gil, Nat. Prod. Commun. 7, 735-738 (2012)
83. V. Schmidts, M. Fredersdorf, T. Lübken, A. Porzel, N. Arnold, L. Wessjohann, C.M. Thiele, J. Nat. Prod. 76, 839-844 (2013)
84. V.M.R. Kakita, K. Rachineni, J. Bharatam, J. Mol. Struct. 1053, 122-126 (2013)
85. K. Huben, M. Jewgiński, A. Pabis, P. Paluch, B. Luy, S. Jankowski, J. Pept. Sci. 20, 901-907 (2014)
86. C.S. Lancefield, A.M.Z. Slawin, N.J. Westwood, T. Lebl, Magn. Reson. Chem. 53, 467-475 (2015)
87. R.R. Teles, J.A.A. França, A. Navarro-Vázquez, F. Hallwass, Quim. Nova 38, 1345-1350 (2015)
88. N. Nath, M. Schmidt, R.R. Gil, R.T. Williamson, G.E. Martin, A. Navarro-Vázquez, C. Griesinger, Y. Liu, J. Am. Chem. Soc. 138, 9548-9556 (2016)
89. L.Y. Liu, H. Sun, C. Griesinger, J.K. Liu, Nat. Prod. Bioprospect. 6, 41-48 (2016)
90. E. Mevers, J. Saurí, Y. Liu, A. Moser, T.R. Ramadhar, M. Varlan, R.T. Williamson, G.E. Martin, J. Clardy, J. Am. Chem. Soc. 138, 12324-12327 (2016)
91. W. Waratchareeyakul, E. Hellemann, R.R. Gil, K. Chantrapromma, M.K. Langat, D.A. Mulholland, J. Nat. Prod. 80, 391-402 (2017)
92. M. Fredersdorf, M. Kurz, A. Bauer, M.O. Ebert, C. Rigling, L. Lannes, C.M. Thiele, Chem. Eur. J. 23, 5729-5735 (2017)
93. Y. Liu, J. Saurí, E. Mevers, M.W. Peczuh, H. Hiemstra, J. Clardy, G.E. Martin, R.T. Williamson, Science. (2017). https://doi.org/10.1126/science.aam5349
94. G. Cornilescu, R.F. Ramos Alvarenga, T.P. Wyche, T.S. Bugni, R.R. Gil, C.C. Cornilescu, W.M. Westler, J.L. Markley, C.D. Schwieters, ACS. Chem. Biol. 12, 2157-2163 (2017)
95. C. Rigling, M.O. Ebert, Magn. Reson. Chem. 55, 655-661 (2017)
96. D.J. Milanowski, N. Oku, L.K. Cartner, H.R. Bokesch, R.T. Williamson, J. Saurí, Y. Liu, K.A. Blinov, Y. Ding, X. Li, D. Ferreira, L.A. Walker, S. Khan, M.T. Davies-Coleman, J.A. Kelley, J.B. McMahon, G.E. Martin, K.R. Gustafson, Chem. Sci. 9, 307-314 (2018)
97. E. Troche-Pesqueira, C. Anklin, R.R. Gil, A. Navarro-Vázquez, Angew. Chem. Int. Ed. 56, 3660-3664 (2017)
98. A. Navarro-Vázquez, R.R. Gil, K. Blinov, J. Nat. Prod. 81, 203-210 (2018)
99. A. Navarro-Vázquez, R. Santamaría-Fernández, F.J. Sardina, Magn. Reson. Chem. 56, 505-512 (2018)
100. F. Hallwass, R.R. Teles, E. Hellemann, C. Griesinger, R.R. Gil, A. Navarro-Vázquez, Magn. Reson. Chem. 56, 321-328 (2018)
101. A. Navarro-Vázquez, P. Berdagué, P. Lesot, ChemPhysChem 18, 1252-1266 (2017)

[1]	Yue-mao Shen, Duo-zhi Chen. An Explorer of Chemical Biology of Plant Natural Products in Southwest China, Xiaojiang Hao[J]. Natural Products and Bioprospecting, 2018, 8(4): 217-226.
[2]	Conrad V. Simoben, Fidele Ntie-Kang, Sergi H. Akone, Wolfgang Sippl. Compounds from African Medicinal Plants with Activities Against Selected Parasitic Diseases: Schistosomiasis, Trypanosomiasis and Leishmaniasis[J]. Natural Products and Bioprospecting, 2018, 8(3): 151-169.
[3]	Ai-Jun Ding, Shan-Qing Zheng, Xiao-Bing Huang, Ti-Kun Xing, Gui-Sheng Wu, Hua-Ying Sun, Shu-Hua Qi, Huai-Rong Luo. Current Perspective in the Discovery of Anti-aging Agents from Natural Products[J]. Natural Products and Bioprospecting, 2017, 7(5): 335-404.
[4]	Rui Chu, Luo-Sheng Wan, Xing-Rong Peng, Mu-Yuan Yu, Zhi-Run Zhang, Lin Zhou, Zhong-Rong Li, Ming-Hua Qiu. *Characterization of New Ent-kaurane Diterpenoids of Yunnan Arabica Coffee Beans*[J]. Natural Products and Bioprospecting, 2016, 6(4): 217-223.
[5]	Fidele Ntie-Kang, Leonel E. Njume, Yvette I. Malange, Stefan Günther, Wolfgang Sippl, Joseph N. Yong. The Chemistry and Biological Activities of Natural Products from Northern African Plant Families: From Taccaceae to Zygophyllaceae[J]. Natural Products and Bioprospecting, 2016, 6(2): 63-96.
[6]	Marie Pascaline Rahelivao, Margit Gruner, Hanta Andriamanantoanina, Ingmar Bauer, Hans-Joachim Knölker. Brown Algae(Phaeophyceae) from the Coast of Madagascar:preliminary Bioactivity Studies and Isolation of Natural Products[J]. Natural Products and Bioprospecting, 2015, 5(5): 223-235.
[7]	Kun Wei, Gang-Qiang Wang, Xue Bai, Yan-Fen Niu, He-Ping Chen, Chun-Nan Wen, Zheng-Hui Li, Ze-Jun Dong, Zhi-Li Zuo, Wen-Yong Xiong, Ji-Kai Liu. Structure-Based Optimization and Biological Evaluation of Pancreatic Lipase Inhibitors as Novel Potential Antiobesity Agents[J]. Natural Products and Bioprospecting, 2015, 5(3): 129-157.
[8]	Frank Surup, Eric Kuhnert, Elena Liscinskij, Marc Stadler. *Silphiperfolene-Type Terpenoids and Other Metabolites from Cultures of the Tropical Ascomycete Hypoxylon rickii(Xylariaceae)*[J]. Natural Products and Bioprospecting, 2015, 5(3): 167-173.
[9]	Joel Heisler, Lindsay Elvir, Farah Barnouti, Erica Charles, Tom D. Wolkow, Radha Pyati. *Morphological Effects of Natural Products on Schizosaccharomyces pombe* Measured by Imaging Flow Cytometry**[J]. Natural Products and Bioprospecting, 2014, 4(1): 27-35.
[10]	Ponnambalam SUBHASHINI, Elangovan DILIPAN, Thirunavukkarasu THANGARADJOU, Jutta PAPENBROCK. Bioactive natural products from marine angiosperms: abundance and functions[J]. Natural Products and Bioprospecting, 2013, 3(4): 129-136.
[11]	Mohammad Mijanur RAHMAN, Md. Asaduzzaman KHAN. Anti-cancer potential of South Asian plants[J]. Natural Products and Bioprospecting, 2013, 3(3): 74-88.
[12]	Steffen WÖLL, Sun Hee KIM, Henry Johannes GRETEN, Thomas EFFERTH. Animal plant warfare and secondary metabolite evolution[J]. Natural Products and Bioprospecting, 2013, 3(1): 1-7.
[13]	Xu DENG, Ling-Mei KONG, Yu ZHAO, Juan HE, Li-Yan PENG, Yan LI, Qin-Shi ZHAO. Exploring of drug leads from diversity-oriented Michael-acceptor library derived from natural products[J]. Natural Products and Bioprospecting, 2012, 2(5): 210-216.
[14]	Hassan KHALID, Wail Elsadig ABDALLA, Haider ABDELGADIR, Till OPATZ, Thomas EFFERTH. Gems from traditional north-African medicine: medicinal and aromatic plants from Sudan[J]. Natural Products and Bioprospecting, 2012, 2(3): 92-103.

Viewed

Full text

Abstract

Cited

Shared

Discussed