Conformational studies of phe-rich foldamers by VCD spectroscopy and ab initio calculations

Journal of Organic Chemistry

Volumn 77, Issue 14, 2012, Pages 6033-6042

  Longhi, Giovanna ^a,b   Abbate, Sergio ^a,b   Lebon, France ^a,b   Castellucci, Nicola ^c   Sabatino, Piera ^c   Tomasini, Claudia ^c  

^a UNIVERSITY OF BRESCIA   (Italy)

^b CNISM   (Italy)

^c UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

AB INITIO CALCULATIONS; COMPUTATIONAL ANALYSIS; CONFORMATIONAL PROPERTIES; CONFORMATIONAL STUDY; FOLDAMERS; IR SPECTRUM; METHANOL SOLUTION; STRUCTURAL BEHAVIORS;

METHANOL; OLIGOMERS;

CALCULATIONS;

CARBON TETRACHLORIDE; METHANOL; OLIGOMER; PHENYLALANINE;

AB INITIO CALCULATION; ARTICLE; CIRCULAR DICHROISM; DENSITY FUNCTIONAL THEORY; ELECTRONIC CIRCULAR DICHROISM SPECTROSCOPY; INFRARED RADIATION; PROTON NUCLEAR MAGNETIC RESONANCE; SPECTROSCOPY; SYNTHESIS; VIBRATIONAL CIRCULAR DICHROISM SPECTROSCOPY;

CIRCULAR DICHROISM; MOLECULAR CONFORMATION; PHENYLALANINE; QUANTUM THEORY;

EID: 84864060920     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo300688n     Document Type: Article

References (65)

1. Hill, D. J.; Mio, M. J.; Prince, R. B.; Hughes, T. S.; Moore, J. S. Chem. Rev. 2001, 101, 3893-4011
2. Foldamers: Structure, Properties, and Applications; Hecht, S.,; Huc, I., Eds.; Wiley-VCH: Weinheim, Germany, 2007.
3. Gellman, S. H. Acc. Chem. Res. 1998, 31, 173-180
4. Martinek, T. A.; Fülöp, F. Chem. Soc. Rev. 2012, 41, 687-702
5. Cubberley, M. S.; Iverson, B. L. Curr. Opin. Chem. Biol. 2001, 5, 650-653
6. Seebach, D.; Beck, A. K.; Bierbaum, D. J. Chem. Biodiversity 2004, 1, 1111-1239
7. Sanford, A.; Yamato, K.; Yang, X. W.; Yuan, L. H.; Han, Y. H.; Gong, B. Eur. J. Biochem. 2004, 271, 1416-1425
8. Cheng, R. P. Curr. Opin. Struct. Biol. 2004, 14, 512-520
9. Balbo Block, M. A.; Kaiser, C.; Khan, A.; Hecht, S. Top. Curr. Chem. 2005, 245, 89-150
10. Goodman, C. M.; Choi, S.; Shandler, S.; DeGrado, W. F. Nat. Chem. Biol. 2007, 3, 252-262
11. Bautista, A. D.; Craig, C. J.; Harker, E. A.; Schepartz, A. Curr. Opin. Chem. Biol. 2007, 11, 685-692
12. Smaldone, R. A.; Moore, J. S. Chem.-Eur. J. 2008, 14, 2650-2657
13. Guichard, G.; Huc, I. Chem. Commun. 2011, 47, 5933-5941
14. Tomasini, C.; Angelici, G.; Castellucci, N. Eur. J. Org. Chem. 2011, 3648-3669
15. Tomasini, C.; Villa, M. Tetrahedron Lett. 2001, 42, 5211-5214
16. Bernardi, F.; Garavelli, M.; Scatizzi, M.; Tomasini, C.; Trigari, V.; Crisma, M.; Formaggio, F.; Peggion, C.; Toniolo, C. Chem.-Eur. J. 2002, 8, 2516-2525
17. Luppi, G.; Soffrè, C.; Tomasini, C. Tetrahedron: Asymmetry 2004, 15, 1645-1650
18. Tomasini, C.; Luppi, G.; Monari, M. J. Am. Chem. Soc. 2006, 128, 2410-2420
19. Angelici, G.; Luppi, G.; Kaptein, B.; Broxterman, Q. B.; Hofmann, H.-J.; Tomasini, C. Eur. J. Org. Chem. 2007, 2713-2721
20. Angelici, G.; Falini, G.; Hofmann, H.-J.; Huster, D.; Monari, M.; Tomasini, C. Angew. Chem., Int. Ed. 2008, 47, 8075-8078
21. Angelici, G.; Falini, G.; Hofmann, H.-J.; Huster, D.; Monari, M.; Tomasini, C. Chem.-Eur. J. 2009, 15, 8037-8048
22. Detoma, A. S.; Salamekh, S.; Ramamoorthy, A.; Lim, M. H. Chem. Soc. Rev. 2012, 41, 608-621
23. Ryan, D. M.; Nilsson, B. L. Polym. Chem. 2012, 3, 18-33
24. Woolfson, D. N. Biopolymers 2010, 94, 118-127
25. Woolfson, D. N.; Ryadnov, M. G. Curr. Opin. Chem. Biol. 2006, 10, 559-567
26. Serpell, L. C. Biochim. Biophys. Acta 2000, 1502, 16-30
27. Ross, C. A.; Poirier, M. A. Nat. Med. (Tokyo, Jpn.) 2004, 10, S10-S17
28. Dalakas, M. C. Neuropathol. Appl. Neurobiol. 2011, 37, 226-242
29. Filosto, M.; Scarpelli, M.; Cotelli, M. S.; Vielmi, V.; Todeschini, A.; Gregorelli, V.; Tonin, P.; Tomelleri, G.; Padovani, A. J. Neurol. 2011, 258, 1763-1774
30. Bekris, L. M.; Bird, C.-E. T. D.; Tsuang, D. W. Journal of Geriatric Psychiatry Neurology 2010, 23, 213-227
31. Colletier, J.-P.; Laganowsky, A.; Landau Meytal, M.; Zhao, M. L.; Soriaga, A. B.; Goldschmidt, L.; Flot, D.; Cascio, D.; Sawaya, M. R.; Eisenberg, D. Proc. Natl. Acad. Sci. U.S.A. 2011, 108, 16938-16943
32. Makin, O. S.; Serpell, L. C. FEBS J. 2005, 272, 5950-5961
33. McLaurin, J.; Yang, D. S.; Yip, C. M.; Fraser, P. E. J. Struct. Biol. 2000, 130, 259-270
34. Tomasini, C.; Trigari, V.; Lucarini, S.; Bernardi, F.; Garavelli, M.; Peggion, C.; Formaggio, F.; Toniolo, C. Eur. J. Org. Chem. 2003, 259-267
35. Belvisi, L.; Gennari, C.; Mielgo, A.; Potenza, D.; Scolastico, C. Eur. J. Org. Chem. 1999, 389-400
36. Yang, J.; Gellman, S. H. J. Am. Chem. Soc. 1998, 120, 9090-9091
37. Jones, I. G.; Jones, W.; North, M. J. Org. Chem. 1998, 63, 1505-1513
38. Toniolo, C.; Benedetti, E. Crit. Rev. Biochem. 1980, 9, 1-44
39. Imperiali, B.; Moats, R. A.; Fisher, S. L.; Prins, T. J. J. Am. Chem. Soc. 1992, 114, 3182-3188
40. Kopple, K. D.; Ohnishi, M.; Go, A. Biochemistry 1969, 8, 4087-4095
41. Martin, D.; Hauthal, G. G. In Dimethyl Sulphoxide; Van Nostrand-Reinhold: Wokingham, U.K., 1975.
42. Stevens, E. S.; Sugawara, N.; Bonora, G. M.; Toniolo, C. J. Am. Chem. Soc. 1980, 102, 7048-7050
43. Sreerama, N.; Manning, M. C.; Powers, M. E.; Zhang, J.-X.; Goldenberg, D. P.; Woody, R. W. Biochemistry 1999, 38, 10814-10822
44. Tatham, A. S.; Drake, A. F.; Shewry, P. R. Biochem. J. 1989, 259, 471-476 and references therein
45. Krysmann, M. J.; Castelletto, V.; McKendrick, J. E.; Clifton, L. A.; Hamley, I. W.; Harris, P. J. F.; King, S. M. Langmuir 2008, 24, 8158-8162
46. Holzwarth, G.; Hsu, E. C.; Mosher, H. S.; Faulkner, T. R.; Moscowitz, A. J. Am. Chem. Soc. 1974, 96, 251-252
47. Sugeta, H.; Marcott, C.; Faulkner, T. R.; Overend, J.; Moscowitz, A. Chem. Phys. Lett. 1976, 40, 397-398
48. Nafie, L. A.; Cheng, J. C.; Stephens, P. J. J. Am. Chem. Soc. 1975, 97, 3842-3843
49. Nafie, L. A.; Keiderling, T. A.; Stephens, P. J. J. Am. Chem. Soc. 1976, 98, 2715-2723
50. Nafie, L. A. Vibrational Optical Activity: Principles and Applications; Wiley: New York, 2011.
51. Stephens, P. J.; Devlin, F. J. Chirality 2000, 12, 172-179
52. Keiderling, T. A. Peptide and Protein Conformational Studies with Vibrational Circular Dichroism and Related Spectroscopies. In Circular Dichroism Principles and Applications, 2 nd ed.; Berova, N.; Nakanishi, K.; Woody, R., Eds.; Wiley-VCH: New York, 2000; pp 621-666.
53. Polavarapu, P. L. Vibrational Spectra and Structure; Bist, H. D.; Durig, J. R.,; Sullivan, J. F., Eds.; Elsevier: Amsterdam, 1989; Vol. 17B, pp 319-342.
54. Uncuta, C.; Bartha, E.; Gherase, D.; Teodorescu, F.; Draghici, C.; Cavagnat, D.; Daugey, N.; Liotard, D.; Buffeteau, T. Chirality 2010, 22, E115-E122
55. Longhi, G.; Abbate, S.; Gangemi, R.; Giorgio, E.; Rosini, C. J. Phys. Chem. A 2006, 110, 4958-4968
56. Abbate, S.; Castiglioni, E.; Gangemi, F.; Gangemi, R.; Longhi, G.; Ruzziconi, R.; Spizzichino, S. J. Phys. Chem. A 2007, 111, 7031-7040
57. Cantor, C. R.; Schimmel, P. R. Biophysical Chemistry; W. H. Freeman and Co.: San Francisco, 1980.
58. Baumruk, V.; Huo, D.; Dukor, R. K.; Keiderling, T. A.; Lelievre, D.; Brack, A. Biopolymers 1994, 34, 1115-1121
59. Keiderling, T. A. Vibrational Circular Dichroism of Proteins. In Spectroscopic Methods for Protein Structure Determination; Havel, H. A., Ed.; Wiley-VCH: New York, 1998.
60. Eker, F.; Gribenow, K.; Cao, X.; Schweitzer-Stenner, R. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 10054-10059
61. Paterlini, M. G.; Freedman, T. B.; Nafie, L. A. Biopolymers 1986, 25, 1751-1765
62. Yasui, S. C.; Keiderling, T. A. J. Am. Chem. Soc. 1986, 108, 5576-5581
63. Dukor, R. K.; Keiderling, T. A. Biopolymers 1991, 31, 1747-1761
64. Reed, J.; Reed, T. A. Anal. Biochem. 1997, 254, 36-40
65. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, Ö.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.;; Fox, D. J. Gaussian 09; revision A.1; Gaussian, Inc.: Wallingford, CT, 2009.