Skip to main content

Application of NOEs and 3JHH-Couplings in 3D Structure Determination

  • Chapter
  • First Online:
Solving a 3D Structural Puzzle

Part of the book series: Springer Theses ((Springer Theses))

  • 349 Accesses

Abstract

Throughout this Chapter, the structural spaces that a multitude of structures inhibits are determined from NOE’s and J-coupling constants. This allow for the elucidation of relative stereochemistry of natural compounds and investigation of 3D structures of synthetic and natural origin.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 84.99
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Hardcover Book
USD 109.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Notes

  1. 1.

    Note that the solvents when acquiring NMR experiments throughout this thesis are always deuterated, unless explicitly stated otherwise.

References

  1. P.M. Dewick, Medicinal Natural Products: A Biosynthetic Approach, 3rd edn. (Wiley, Hoboken, 2009)

    Book  Google Scholar 

  2. N.P. Keller, G. Turner, J.W. Bennett, Nat. Rev. Microbiol. 3, 937–947 (2005)

    Article  CAS  Google Scholar 

  3. F. Kempken, M. Rohlfs, Fungal Ecol. 3, 107–114 (2010)

    Article  Google Scholar 

  4. A.M. Calvo, R.A. Wilson, J.W. Bok, N.P. Keller, Microbiol. Mol. Biol. Rev. 66, 447–459 (2002)

    Article  CAS  Google Scholar 

  5. D.J. Newman, G.M. Cragg, J. Nat. Prod. 79, 629–661 (2016)

    Article  CAS  Google Scholar 

  6. P.D. Leeson, B. Springthorpe, Nat. Rev. Drug Discov. 6, 881–890 (2007)

    Article  CAS  Google Scholar 

  7. J.L. Meier, M.D. Burkart, Chem. Soc. Rev. 38, 2012–2045 (2009)

    Article  CAS  Google Scholar 

  8. M.A. Fischbach, C.T. Walsh, Chem. Rev. 106, 3468–3496 (2006)

    Article  CAS  Google Scholar 

  9. T. Weber, H.U. Kim, Synth. Syst. Biotechnol. 1, 69–79 (2016)

    Article  Google Scholar 

  10. J. Varga, J.C. Frisvad, S. Kocsubé, B. Brankovics, B. Tóth, G. Szigeti, R.A. Samson, Stud. Mycol. 69, 1–17 (2011)

    Article  CAS  Google Scholar 

  11. K.F. Nielsen, J.M. Mogensen, M. Johansen, T.O. Larsen, J.C. Frisvad, Anal. Bioanal. Chem. 395, 1225–1242 (2009)

    Article  CAS  Google Scholar 

  12. R. Steiman, P. Guiraud, L. Sage, F. Seigle-Murandi, Syst. Appl. Microbiol. 17, 620–624 (1995)

    Article  Google Scholar 

  13. M.L. Chiotta, A. Susca, G. Stea, G. Mulè, G. Perrone, A. Logrieco, S.N. Chulze, Int. J. Food Microbiol. 149, 171–176 (2011)

    Article  CAS  Google Scholar 

  14. R.A. Samson, P. Noonim, M. Meijer, J. Houbraken, J.C. Frisvad, J. Varga, Stud. Mycol. 59, 129–145 (2007)

    Article  CAS  Google Scholar 

  15. J.M. Berg, J.L. Tymoczko, L. Stryer, Biochemistry, 6th edn. (W. H. Freeman and Company, New York, 2007)

    Google Scholar 

  16. Y.N. Han, K.H. Hwang, B.H. Han, Arch. Pharm. Res. 28, 159–163 (2005)

    Article  CAS  Google Scholar 

  17. K.H. Hwang, Y.N. Han, B.H. Han, Arch. Pharm. Res. 24, 202–206 (2001)

    Article  CAS  Google Scholar 

  18. A.F. Morel, E.C. Machado, L.A. Wessjohann, Phytochemistry 39, 431–434 (1995)

    Article  CAS  Google Scholar 

  19. M.A. Mostardeiro, V. Ilha, J. Dahmer, M.S.B. Caro, I.I. Dalcol, U.F. da Silva, A.F. Morel, J. Nat. Prod. 76, 1343–1350 (2013)

    Article  CAS  Google Scholar 

  20. M.H. Park, D.-Y. Suh, B.H. Han, Phytochemistry 43, 701–704 (1996)

    Article  CAS  Google Scholar 

  21. C.T. Walsh, R.V. O’Brien, C. Khosla, Angew. Chem. Int. Ed. Engl. 52, 7098–7124 (2015)

    Article  Google Scholar 

  22. M. Köck, G. Schmidt, I.B. Seiple, P.S. Baran, J. Nat. Prod. 75, 127–130 (2012)

    Article  Google Scholar 

  23. R. Bhushan, H. Brückner, Amino Acids 27, 231–247 (2004)

    Article  CAS  Google Scholar 

  24. P. Marfey, Carlsberg Res. Commun. 49, 591–596 (1984)

    Article  CAS  Google Scholar 

  25. W.K. Wilson, R.M. Sumpter, J.J. Warren, P.S. Rogers, B. Ruan, G.J. Schroepfer Jr., J. Lipid Res. 37, 1529–1555 (1996)

    CAS  PubMed  Google Scholar 

  26. S.G. Smith, J.M. Goodman, J. Am. Chem. Soc. 132, 12946–12959 (2010)

    Article  CAS  Google Scholar 

  27. L.W. Parks, W.M. Casey, Annu. Rev. Microbiol. 49, 95–116 (1995)

    Article  CAS  Google Scholar 

  28. Y. Zhang, X.-M. Li, P. Proksch, B.-G. Wang, Steroids 72, 723–727 (2007)

    Article  Google Scholar 

  29. R. Jain, T. Bally, P.R. Rablen, J. Org. Chem. 74, 4017–4023 (2009)

    Article  CAS  Google Scholar 

  30. M.W. Lodewyk, M.R. Siebert, D.J. Tantillo, Chem. Rev. 112, 1839–1862 (2012)

    Article  CAS  Google Scholar 

  31. L.M. Petersen, C. Hoeck, J.C. Frisvad, C.H. Gotfredsen, T.O. Larsen, Molecules 19, 10898–10921 (2014)

    Article  CAS  Google Scholar 

  32. M.R. TePaske, J.B. Gloer, Tetrahedron 45, 4961–4968 (1989)

    Article  CAS  Google Scholar 

  33. J.B. Gloer, M.R. Tepaske, J.S. Sima, D.T. Wicklow, P.F. Dowd, J. Org. Chem. 53, 5457–5460 (1988)

    Article  CAS  Google Scholar 

  34. A.R. Maolanon, J.S. Villadsen, N.J. Christensen, C. Hoeck, T. Friis, P. Harris, C.H. Gotfredsen, P. Fristrup, C.A. Olsen, J. Med. Chem. 57, 9644–9657 (2014)

    Article  CAS  Google Scholar 

  35. M. Li, C. Hoeck, S. Schoffelen, C.H. Gotfredsen, M. Meldal, Chem. Eur. J. 22, 7206–7214 (2016)

    Article  CAS  Google Scholar 

  36. Y. Nakao, S. Yoshida, S. Matsunaga, N. Shindoh, Y. Terada, K. Nagai, J.K. Yamashita, A. Ganesan, R.W.M. Van Soest, N. Fusetani, Angew. Chemie 118, 7715–7719 (2006)

    Article  Google Scholar 

  37. P. Bertrand, Eur. J. Med. Chem. 45, 2095–2116 (2010)

    Article  CAS  Google Scholar 

  38. A.J.M. de Ruijter, A.H. van Gennip, H.N. Caron, S. Kemp, A.B.P. van Kuilenburg, Biochem. J. 370, 737–749 (2003)

    Article  Google Scholar 

  39. I. Izzo, N. Maulucci, G. Bifulco, F. De Riccardis, Angew. Chemie 118, 7719–7722 (2006)

    Article  Google Scholar 

  40. N. Maulucci, M.G. Chini, S. Di, I. Izzo, E. Cafaro, A. Russo, P. Gallinari, C. Paolini, M.C. Nardi, A. Casapullo, R. Riccio, G. Bifulco, F. De Riccardis, J. Am. Chem. Soc. 129, 3007–3012 (2007)

    Article  CAS  Google Scholar 

  41. B. Vögeli, P. Güntert, R. Riek, Mol. Phys. 111, 437–454 (2013)

    Article  Google Scholar 

  42. Y. Levy, N. Onuchic, Annu. Rev. Biophys. Biomol. Struct. 35, 389–415 (2006)

    Article  CAS  Google Scholar 

  43. G.R. Crabtree, N.A. Clipstone, Annu. Rev. Biochem. 63, 1045–1083 (1994)

    Article  CAS  Google Scholar 

  44. E.J. Sundberg, R.A. Mariuzza, Adv. Protein Chem. 61, 119–160 (2002)

    Article  Google Scholar 

  45. R.E. Babine, S.L. Bender, Chem. Rev. 97, 1359–1472 (1997)

    Article  CAS  Google Scholar 

  46. M. Renil, M. Ferreras, J.M. Delaisse, N.T. Foged, M. Meldal, J. Pept. Sci. 4, 195–210 (1998)

    Article  CAS  Google Scholar 

  47. M. Meldal, B. Wu, F. Diness, R. Michael, G. Hagel, ChemBioChem 12, 2463–2470 (2011)

    Article  CAS  Google Scholar 

  48. E.P. Diamandis, T.K. Christopoulos, Clin. Chem. 37, 625–636 (1991)

    CAS  PubMed  Google Scholar 

  49. B.W. Sigurskjolds, D.R. Bundle, J. Biol. Chem. 267, 8371–8376 (1992)

    Google Scholar 

  50. H. Kaur, M. Datt, M.K. Ekka, M. Mittal, A.K. Singh, S. Kumaran, Biochimie 93, 175–186 (2011)

    Article  CAS  Google Scholar 

  51. S. Sasaki, M. Takagi, Y. Tanaka, M. Maeda, Tetrahedron Lett. 37, 85–88 (1996)

    Article  CAS  Google Scholar 

  52. T. Young, R. Abel, B. Kim, B.J. Berne, R.A. Friesner, Proc. Natl. Acad. Sci. U.S.A. 104, 808–813 (2007)

    Article  CAS  Google Scholar 

  53. S. Macura, B.T. Farmer II, L.R. Brown, J. Magn. Reson. 70, 493–499 (1986)

    CAS  Google Scholar 

  54. P. Thordarson, Chem. Soc. Rev. 40, 1305–1323 (2011)

    Article  CAS  Google Scholar 

  55. J.N.S. Evans, Biomolecular NMR Spectroscopy, 1st edn. (Oxford University Press, Oxford, 1995)

    Google Scholar 

  56. T. Burgi, A. Baiker, J. Am. Chem. Soc. 120, 12920–12926 (1998)

    Article  Google Scholar 

  57. J.T. Kowalik, T. Lipinska, B.J. Oleksyn, J. Sliwinski, Enantiomer 4, 389–410 (1999)

    CAS  PubMed  Google Scholar 

  58. G.D.H. Dijkstra, R.M. Kellogg, H. Wynberg, J. Org. Chem. 55, 6121–6131 (1990)

    Article  CAS  Google Scholar 

  59. E.M.O. Yeboah, S.O. Yeboah, G.S. Singh, Tetrahedron 67, 1725–1762 (2011)

    Article  CAS  Google Scholar 

  60. T.H.A. Silva, A.B. Oliveira, W.B. De Almeida, Struct. Chem. 8, 95–107 (1997)

    Article  CAS  Google Scholar 

  61. A. Sen, A. Bouchet, V. Lepe, K. Le Barbu-debus, D. Scuderi, F. Piuzzi, A. Zehnacker-Rentien, J. Phys. Chem. A 116, 8334–8344 (2012)

    Article  CAS  Google Scholar 

  62. A. Urakawa, D.M. Meier, H. Rüegger, A. Baiker, J. Phys. Chem. A 112, 7250–7255 (2008)

    Article  CAS  Google Scholar 

  63. S.V. Efimov, I.A. Khodov, E.L. Ratkova, M.G. Kiselev, S. Berger, V.V. Klochkov, J. Mol. Struct. 1104, 63–69 (2016)

    Article  CAS  Google Scholar 

  64. R. Pendrill, E. Säwén, G. Widmalm, J. Phys. Chem. B 117, 14709–14722 (2013)

    Article  CAS  Google Scholar 

  65. H. Kessler, C. Griesinger, R. Kerssebaum, K. Wagner, R.R. Ernst, J. Am. Chem. Soc. 109, 607–609 (1987)

    Article  CAS  Google Scholar 

  66. M. Mackeen, A. Almond, I. Cumpstey, S.C. Enis, E. Kupce, T.D. Butters, A.J. Fairbanks, R.A. Dwek, M.R. Wormald, Org. Biomol. Chem. 4, 2241–2246 (2006)

    Article  CAS  Google Scholar 

  67. A. Kjellberg, G. Widmalm, Biopolymers 50, 391–399 (1999)

    Article  CAS  Google Scholar 

  68. X. Mao, T. Zhang, M. Baur, H. Kessler, J. Chem. Phys. 111, 8253–8254 (1999)

    Article  CAS  Google Scholar 

  69. D. Neuhaus, M. Williamson, The Nuclear Overhauser Effect in Structural and Conformational Analysis, 1st edn. (VCH Publishers, Weinheim, 1989)

    Google Scholar 

  70. D. Lee, C. Hilty, G. Wider, K. Wüthrich, J. Magn. Reson. 178, 72–76 (2006)

    Article  CAS  Google Scholar 

  71. T.-L. Hwang, M. Kadkhodaei, A. Mohebbi, A.J. Shaka, Magn. Reson. Chem. 30, S24–S34 (1992)

    Article  CAS  Google Scholar 

  72. T.-L. Hwang, A.J. Shaka, J. Am. Chem. Soc. 114, 3157–3159 (1992)

    Article  CAS  Google Scholar 

  73. U. Olsson, E. Säwën, R. Stenutz, G. Widmalm, Chem. Eur. J. 15, 8886–8894 (2009)

    Article  CAS  Google Scholar 

  74. Maestro (Schrödinger, LLC, New York, 2015)

    Google Scholar 

  75. Schrödinger (LLC, New York, NY 2016)

    Google Scholar 

  76. Desmond (D. E. Shaw Research, New York, 2015)

    Google Scholar 

  77. G. Chang, W.C. Guida, W.C. Still, J. Am. Chem. Soc. 111, 4379–4386 (1989)

    Article  CAS  Google Scholar 

  78. I. Chen, N. Foloppe, Bioorg. Med. Chem. 21, 7898–7920 (2013)

    Article  CAS  Google Scholar 

  79. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H.P. Hratchian, A.F. Izmaylov, J. Bloino, G. Zheng, J.L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J.A. Montgomery Jr., J.E. Peralta, F. Ogliaro, M. Bearpark, J.J. Heyd, E. Brothers, K.N. Kudin, V.N. Staroverov, T. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J.M. Millam, M. Klene, J.E. Knox, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, R.L. Martin, K. Morokuma, V.G. Zakrzewski, G.A. Voth, P. Salvador, J.J. Dannenberg, S. Dapprich, A.D. Daniels, O. Farkas, J.B. Foresman, J.V. Ortiz, J. Cioslowski, D.J. Fox, in Gaussian 09, Revision B.01 (Gaussian Inc., Wallingford, CT, 2010)

    Google Scholar 

  80. C.R. Jones, C.P. Butts, J.N. Harvey, Beilstein J. Org. Chem. 7, 145–150 (2011)

    Article  CAS  Google Scholar 

  81. C.P. Butts, C.R. Jones, Z. Song, T.J. Simpson, Chem. Commun. 48, 9023–9025 (2012)

    Article  CAS  Google Scholar 

  82. C.P. Butts, C.R. Jones, E.C. Towers, J.L. Flynn, L. Appleby, N.J. Barron, Org. Biomol. Chem. 9, 177–184 (2011)

    Article  CAS  Google Scholar 

  83. C.P. Butts, C.R. Jones, J.N. Harvey, Chem. Commun. 47, 1193–1195 (2011)

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Casper Rønn Hoeck .

Rights and permissions

Reprints and permissions

Copyright information

© 2018 Springer International Publishing AG, part of Springer Nature

About this chapter

Check for updates. Verify currency and authenticity via CrossMark

Cite this chapter

Hoeck, C.R. (2018). Application of NOEs and 3JHH-Couplings in 3D Structure Determination. In: Solving a 3D Structural Puzzle. Springer Theses. Springer, Cham. https://doi.org/10.1007/978-3-319-96172-9_3

Download citation

Publish with us

Policies and ethics