Residual Dipolar Couplings in Structure Determination of Natural Products

doi:10.1007/s13659-018-0174-x

应用天然产物 ›› 2018, Vol. 8 ›› Issue (4): 279-295.DOI: 10.1007/s13659-018-0174-x

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

收稿日期:2018-05-28 修回日期:2018-06-14 出版日期:2018-08-24 发布日期:2018-08-28
通讯作者: Xin-Xiang Lei,xxlei@mail.scuec.edu.cn
基金资助:
The project was financially co-supported by National Natural Science Foundation of China (21572164, U1504207) and the Sino-German Center for Research Promotion (GZ1289).

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

Received:2018-05-28 Revised:2018-06-14 Online:2018-08-24 Published:2018-08-28
Contact: Xin-Xiang Lei,xxlei@mail.scuec.edu.cn
Supported by:
The project was financially co-supported by National Natural Science Foundation of China (21572164, U1504207) and the Sino-German Center for Research Promotion (GZ1289).

摘要/Abstract

摘要： 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.

关键词: NMR spectroscopy, Residual dipolar couplings, Alignment media, Structural elucidation, Natural products

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.

Key words: NMR spectroscopy, Residual dipolar couplings, Alignment media, Structural elucidation, Natural products

Gao-Wei Li, Han Liu, Feng Qiu, Xiao-Juan Wang, Xin-Xiang Lei. Residual Dipolar Couplings in Structure Determination of Natural Products[J]. 应用天然产物, 2018, 8(4): 279-295.

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

参考文献

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]	Pengkun Li, Qin Li, Aimin Fu, Yang Xiao, Chunmei Chen, Hucheng Zhu, Changxing Qi, Wei Wei, Yuan Zhou, Yonghui Zhang. Emestrin-type epipolythiodioxopiperazines from Aspergillus nidulans with cytotoxic activities by regulating PI3K/AKT and mitochondrial apoptotic pathways[J]. 应用天然产物, 2025, 15(2): 17-17.
[2]	Hesham R. El-Seedi, Mohamed S. Refaey, Nizar Elias, Mohamed F. El-Mallah, Faisal M. K. Albaqami, Ismail Dergaa, Ming Du, Mohamed F. Salem, Haroon Elrasheid Tahir, Maria Dagliaa, Nermeen Yosri, Hongcheng Zhang, Awg H. El-Seedi, Zhiming Guo, Shaden A. M. Khalifa. Marine natural products as a source of novel anticancer drugs: an updated review (2019-2023)[J]. 应用天然产物, 2025, 15(2): 13-13.
[3]	María I. Osella, Mario O. Salazar, Carlos M. Solís, Ricardo L. E. Furlan. New semisynthetic α-glucosidase inhibitor from a doubly-chemically engineered extract[J]. 应用天然产物, 2025, 15(1): 4-4.
[4]	Ahmed H. Elbanna, Xinhui Kou, Dilip V. Prajapati, Surasree Rakshit, Rebecca A. Butcher. Discovery of a parallel family of euglenatide analogs in Euglena gracilis[J]. 应用天然产物, 2025, 15(1): 10-10.
[5]	Song-Yu Hou, Bing-Chao Yan, Han-Dong Sun, Pema-Tenzin Puno. Recent advances in the application of [2+2] cycloaddition in the chemical synthesis of cyclobutane-containing natural products[J]. 应用天然产物, 2024, 14(5): 37-37.
[6]	Felaine Anne Sumang, Alan Ward, Jeff Errington, Yousef Dashti. Hibiscus acid and hydroxycitric acid dimethyl esters from Hibiscus flowers induce production of dithiolopyrrolone antibiotics by Streptomyces Strain MBN2-2[J]. 应用天然产物, 2024, 14(5): 40-40.
[7]	Chunsong Hu. Marine natural products and human immunity: novel biomedical resources for anti-infection of SARS-CoV-2 and related cardiovascular disease[J]. 应用天然产物, 2024, 14(2): 2-2.
[8]	Shohreh Ariaeenejad, Javad Gharechahi, Mehdi Foroozandeh Shahraki, Fereshteh Fallah Atanaki, Jian-Lin Han, Xue-Zhi Ding, Falk Hildebrand, Mohammad Bahram, Kaveh Kavousi, Ghasem Hosseini Salekdeh. Precision enzyme discovery through targeted mining of metagenomic data[J]. 应用天然产物, 2024, 14(1): 7-7.
[9]	Daniel W. Armstrong, Alain Berthod. Occurrence of D-amino acids in natural products[J]. 应用天然产物, 2023, 13(6): 47-47.
[10]	Dalila Carbone, Carmela Gallo, Genoveffa Nuzzo, Giusi Barra, Mario Dell'Isola, Mario Affuso, Olimpia Follero, Federica Albiani, Clementina Sansone, Emiliano Manzo, Giuliana d'Ippolito, Angelo Fontana. Marine natural product lepadin A as a novel inducer of immunogenic cell death via CD91-dependent pathway[J]. 应用天然产物, 2023, 13(5): 34-34.
[11]	Phanankosi Moyo, Luke Invernizzi, Sephora M. Mianda, Wiehan Rudolph, Warren A. Andayi, Mingxun Wang, Neil R. Crouch, Vinesh J. Maharaj. Leveraging off higher plant phylogenetic insights for antiplasmodial drug discovery[J]. 应用天然产物, 2023, 13(5): 35-35.
[12]	Phanankosi Moyo, Luke Invernizzi, Sephora M. Mianda, Wiehan Rudolph, Andrew W. Andayi, Mingxun Wang, Neil R. Crouch, Vinesh J. Maharaj. Prioritised identification of structural classes of natural products from higher plants in the expedition of antimalarial drug discovery[J]. 应用天然产物, 2023, 13(5): 37-37.
[13]	Fengli Li, Saisai Gu, Sitian Zhang, Shuyuan Mo, Jieru Guo, Zhengxi Hu, Yonghui Zhang. Three new amide derivatives from the fungus Alternaria brassicicola[J]. 应用天然产物, 2023, 13(4): 28-28.
[14]	Shuyuan Mo, Ziming Zhao, Zi Ye, Zhihong Huang, Yaxin Zhang, Wanqi Yang, Jianping Wang, Zhengxi Hu, Yonghui Zhang. New secondary metabolites with cytotoxicity from fungus Penicillium roqueforti[J]. 应用天然产物, 2023, 13(3): 17-17.
[15]	Ji-Kai Liu. Natural products in cosmetics[J]. 应用天然产物, 2022, 12(6): 40-40.

Residual Dipolar Couplings in Structure Determination of Natural Products

Residual Dipolar Couplings in Structure Determination of Natural Products

PDF (PC)

可视化

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 15

编辑推荐

Metrics

本文评价