Predicting cyclic peptide chemical shifts using quantum mechanical calculations

Tetrahedron

Volumn 70, Issue 42, 2014, Pages 7655-7663

  Zaretsky, Serge ^a   Hickey, Jennifer L ^b   St Denis, Megan A ^b   Scully, Conor C G ^a   Roughton, Andrew L ^b   Tantillo, Dean J ^c   Lodewyk, Michael W ^c   Yudin, Andrei K ^a  

^a UNIVERSITY OF TORONTO   (Canada)

^b Encycle Therapeutics Inc   (Canada)

^c UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Chemical shift prediction; Cyclic peptides; Macrocycles; NMR

Indexed keywords

ALDEHYDE DERIVATIVE; AZIRIDINE DERIVATIVE; CYCLOPEPTIDE; DIMETHYL SULFOXIDE; ISOCYANIC ACID DERIVATIVE;

AB INITIO CALCULATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CORRELATION SPECTROSCOPY; CYCLIZATION; DENSITY FUNCTIONAL THEORY; GEOMETRY; HETERONUCLEAR MULTIPLE BOND CORRELATION; HETERONUCLEAR SINGLE QUANTUM COHERENCE; MACROCYCLIZATION; MONTE CARLO METHOD; PREDICTION; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTUM MECHANICS; SPECTROSCOPY;

EID: 84907930136     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2014.07.070     Document Type: Article

References (54)

1. D.S. Wishart, and A.M. Nip Biochem. Cell Biol. 76 1998 153
2. H. Kessler Angew. Chem., Int. Ed. Engl. 21 1982 512
3. Y. Wang, and O. Jardetzky Protein Sci. 11 2002 852
4. A.C. Gibbs, L.H. Kondejewski, W. Gronwald, A.M. Nip, R.S. Hodges, B.D. Sykes, and D.S. Wishart Nat. Struct. Biol. 5 1998 284
5. D.S. Wishart, B.D. Sykes, and F.M. Richards J. Mol. Biol. 222 1991 311
6. S.R. Adusumalli, A.K. Yudin, and V. Rai Cyclic Peptides T. Janecki, Natural Lactones and Lactams. Synthesis, Occurrence and Biological Activity 2013 Wiley-VCH Weinheim, Germany 321 369
7. Y. Takada, M. Umehara, R. Katsumata, Y. Nakao, and J. Kimura Tetrahedron 68 2012 659
8. J.M. Crawford, C. Portmann, R. Kontnik, C.T. Walsh, and J. Clardy Org. Lett. 13 2011 5144
9. K. Hung, P.W.R. Harris, A.M. Heapy, and M.A. Brimble Org. Biomol. Chem. 9 2011 236
10. G. Lang, T. Kalvelage, A. Peters, J. Wiese, and J.F. Imhoff J. Nat. Prod. 71 2008 1074
11. J.S. Davies J. Pept. Sci. 9 2003 471
12. L. Zhang, and J.P. Tam J. Am. Chem. Soc. 121 1999 3311
13. U. Schmidt, and J. Langner J. Pept. Res. 49 1997 67
14. A. Ehrlich, H.-U. Heyne, R. Winter, M. Beyermann, H. Haber, L.A. Carpino, and M. Bienert J. Org. Chem. 61 1996 8831
15. M. Umehara, T. Negishi, Y. Maehara, Y. Nakao, and J. Kimura Tetrahedron 69 2013 3045
16. Chem Office, CambridgeSoft Corp., 100 Cambridge Park Drive, Cambridge, MA 02140-9802, USA.
17. ACD, Advanced Chemistry Development, Inc., 8 King Street East, Suite 107, Toronto, Ontario, Canada M5C 1B5.
18. P.H. Willoughby, M.J. Jansma, and T.R. Hoye Nat. Protoc. 9 2014 643
19. K.J. Kohlhoff, P. Robustelli, A. Cavalli, X. Salvatella, and M. Vendruscolo J. Am. Chem. Soc. 131 2009 13894
20. B. Han, Y. Liu, S. Ginzinger, and D.S. Wishart J. Biomol. NMR 50 2011 43
21. Y. Shen, and A. Bax J. Biomol. NMR 48 2010 13
22. C.V. Sumowski, M. Hanni, S. Schweizer, and C. Ochsenfeld J. Chem. Theory Comput. 10 2014 122
23. F.V. Toukach, and V.P. Ananikov Chem. Soc. Rev. 42 2013 8376
24. D.J. Tantillo Nat. Prod. Rep. 30 2013 1079
25. E. Pauwels, D. Claeys, J.C. Martins, M. Waroquier, G. Bifulco, V. Van Speybroeck, and A. Madder RSC Adv. 3 2013 3925
26. M.W. Lodewyk, M.R. Siebert, and D.J. Tantillo Chem. Rev. 112 2012 183
27. S. Di Micco, M.G. Chini, R. Riccio, and G. Bifulco Eur. J. Org. Chem. 8 2010 1411
28. A. Bagno, and G. Saielli Theor. Chem. Acc. 117 2007 603
29. G. Bifulco, P. Dambruoso, L. Gomez-Paloma, and R. Riccio Chem. Rev. 107 2007 3744
30. E.V. Mercado-Marin, P. Garcia-Reynaga, S. Romminger, E.F. Pimenta, D.K. Romney, M.W. Lodewyk, D.E. Williams, R.J. Andersen, S.J. Miller, D.J. Tantillo, R.G.S. Berlinck, and R. Sarpong Nature 509 2014 318
31. T.P. Lebold, J.L. Wood, J. Deitch, M.W. Lodewyk, D.J. Tantillo, and R. Sarpong Nat. Chem. 5 2013 126
32. M.W. Lodewyk, C. Soldi, P.B. Jones, M.M. Olmstead, J.R. Larrucea, J.T. Shaw, and D.J. Tantillo J. Am. Chem. Soc. 134 2012 18550
33. A.M. Sarotti Org. Biomol. Chem. 11 2013 4847
34. S.G. Smith, and J.M. Goodman J. Am. Chem. Soc. 132 2010 12946
35. S.G. Smith, and J.M. Goodman J. Org. Chem. 74 2009 4597
36. R. Hili, V. Rai, and A.K. Yudin J. Am. Chem. Soc. 132 2010 2889
37. S. Zaretsky, C.C.G. Scully, A.J. Lough, and A.K. Yudin Chem. - Eur. J. 19 2013 17668
38. Spartan'10; Wavefunction, Inc., Irvine, CA, USA.
39. M.J. Vainia, J.S. Puranen, and M.S. Johnson J. Chem. Inf. Model. 49 2009 492 www.abo.fi/∼mivainio/shaep/
40. 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, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, N. Rega, N.J. 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, Ö. Farkas, J.B. Foresman, J.V. Ortiz, J. Cioslowski, and D.J. Fox Gaussian 09, Revision B.01 2009 Gaussian, Inc. Wallingford CT
41. http://cheshirenmr.info.
42. T. Bally, and P.R. Rablen J. Org. Chem. 76 2011 4818
43. R. Jain, T. Bally, and P.R. Rablen J. Org. Chem. 74 2009 4017
44. A.M. Sarotti, and S.C. Pellegrinet J. Org. Chem. 77 2012 6059
45. A.M. Sarotti, and S.C. Pellegrinet J. Org. Chem. 74 2009 7254
46. B.H. Rotstein, V. Rai, R. Hili, and A.K. Yudin Nat. Protoc. 5 2010 1813
47. R. Hili, and A.K. Yudin J. Am. Chem. Soc. 128 2006 14772
48. N-Methylacetamide experimental shift values obtained from H. Fritz, H. Kristinsson, M. Mollenkopf, and T. Winkler Magn. Reson. Chem. 28 1990 331
49. J.R. Cheeseman, G.W. Trucks, T.A. Keith, and M.J. Frisch J. Chem. Phys. 104 1996 5497
50. K. Wolinski, J.F. Hilton, and P. Pulay J. Am. Chem. Soc. 112 1990 8251
51. R. Ditchfield Mol. Phys. 27 1974 789
52. R. McWeeny Phys. Rev. 126 1962 1028
53. F. London J. Phys. Radium 8 1937 397
54. A.V. Marenich, C.J. Cramer, and D.G. Truhlar J. Phys. Chem. B 113 2009 6378