Influence of solvents on conformation of dehydropeptides

Journal of Molecular Structure

Volumn 1035, Issue , 2013, Pages 129-139

  Jewginski, Michal ^a   Latajka, Rafal ^a   Krezel, Artur ^b   Haremza, Kinga ^a   Makowski, MacIej ^c   Kafarski, Pawel ^a  

^a WROCLAW UNIVERSITY OF TECHNOLOGY   (Poland)

^b UNIVERSITY OF WROC AW   (Poland)

^c UNIVERSITY OF OPOLE   (Poland)

Author keywords

Circular dichroism; Dehydropeptide; Dehydropeptide conformation; Dehydrophenylalanine; NMR; Solvent polarity

Indexed keywords

AB INITIO METHOD; CONFORMATIONAL ANALYSIS; DEHYDROPEPTIDE; DEHYDROPEPTIDES; DEHYDROPHENYLALANINE; HEXAPEPTIDE; INTRA-MOLECULAR HYDROGEN BONDS; MAIN CHAINS; MOLECULAR MODELING TECHNIQUES; PEPTIDE CHAIN; SIDE-CHAINS; SOLVENT INFLUENCE; SOLVENT POLARITY; SPECTROSCOPIC METHOD; STRUCTURAL INVESTIGATION; TRIPEPTIDE;

AMINO ACIDS; CONFORMATIONS; DICHROISM; NUCLEAR MAGNETIC RESONANCE; SPECTROSCOPIC ANALYSIS;

SOLVENTS;

EID: 84867320474     PISSN: 00222860     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molstruc.2012.08.042     Document Type: Article

References (61)

1. M. Thormann, and H.-J. Hofmann J. Mol. Struct. (Theochem) 431 1998 79 96
2. A.K. Fuzery, and I.G. Csizmadia J. Mol. Struct. (Thoechem) 501-502 2000 539 547
3. K. Tori, K. Tokura, K. Okabe, and M.H.O. Ebata Tetrahedron Lett. 17 1976 185 188
4. K.R. Rajashankar, S. Ramakumar, and V.S. Chauhan J. Am. Chem. Soc. 1992 114
5. T.K. Mal, R.M. Jain, V.S. Chauchan, and K.R.S.R. Rajashankar Angew. Chem. Int. Ed. Engl. 35 1996 765 768
6. R.M. Jain, M. Singh, and V.S. Chauhan Tetrahedron 1994 50
7. U.A. Ramagopal, R.S. Ramakumar, R.M. Joshi, and V.S. Chauchan J. Peptide Res. 52 1998 208 215
8. G.B.R. Pietrzynski, and M. Kubica Int. J. Pept. Prot. Res. 40 1992 524 531
9. G.B.R. Pietrzynski, E. Ciszak, M. Lisowski, M. Kubica, and G. Boussard Int. J. Pept. Prot. Res. 1996 48
10. M. Lisowski, and G.B.R. Pietrzynski Int. J. Pept. Prot. Res. 42 1993 466 474
11. R. Latajka, M. Jewginski, M. Makowski, M. Pawelczak, T. Huber, N. Sewald, and P. Kafarski J. Pept. Sci. 14 2008 1084 1095
12. R. Latajka, M. Jewginski, M. Makowski, A. Krezel, and S. Paluch Biopolymers 89 2008 691 699
13. P.K.U. Kaur, P. Balaram, and V.S. Chauchan Int. J. Pept. Prot. Res. 33 1989 103 109
14. V. Busetti, M. Crisma, C. Toniolo, S. Salvadori, and G. Balboni Int. J. Biol. Macromol. 14 1992 23 28
15. M.S.C. Pedras, J.L. Taylor, and T.T. Nakashima J. Org. Chem. 58 1993 4778 4780
16. V.S. Chauchan, K. Ashwanik, A.K.K.U. Sharma, P.K.C. Paul, and P. Balaram Int. J. Pept. Prot. Res. 29 1987 126 133
17. S. Dey, S.N. Mitra, and T.P. Singh Int. J. Pept. Prot. Res. 48 1996 123 128
18. V.K. Goel, R.K. Somvanshi, S. Dey, and T.P. Singh Struct. Chem. 16 2005 385 389
19. R. Latajka, M. Makowski, M. Jewginski, M. Pawelczak, H. Koroniak, and P. Kafarski New J. Chem. 30 2006 1009 1018
20. R. Latajka, M. Jewginski, M. Makowski, and A. Krezel J. Mol. Struct. 892 2008 446 451
21. G. Hungeford, M. Martinez-Insua, D.J.S. Birch, and B.D. Moore Angew. Chem. Int. Ed. Engl. 35 1996 326 329
22. G. Yoder, A. Polese, R.A.G.D. Silva, F. Formaggio, M. Crisma, Q.B. Broxterman, J. Kamphuis, C. Toniolo, and T.A. Keiderling J. Am. Chem. Soc. 1997 119
23. T.S. Yokum, T.J. Gauthier, R.P. Hammer, and M.L. McLaughlin J. Am. Chem. Soc. 119 1997 1167 1168
24. P. Pengo, L. Pasquato, S. Moro, A. Brigo, and F. Fogolari Angew. Chem. Int. Ed. Engl. 42 2003 3388 3392
25. Z. Liu, K. Chen, A. Ng, Z. Shi, R.W. Woody, and N.R. Kallenbach J. Am. Chem. Soc. 2004 126
26. Y. Inai, S. Kurashima, T. Hirabayashi, and K. Yokota Biopolymers 53 2000 484 496
27. M. Lisowski, R. Latajka, B. Picur, T. Lis, I. Bryndal, M. Rospenk, M. Makowski, and P. Kafarski Biopolymers 89 2008 220 234
28. O. Pieroni, A. Fissi, C. Pratesi, P.A. Temussi, and F. Ciardelli Biopolymers 33 1993 1 10
29. Y. Inai, Y. Kurokawa, and T. Hirabayashi Biopolymers 49 1999 551 564
30. R.M. Jain, K.R. Rajashankar, S. Ramakumar, and V.S. Chauhan J. Am. Chem. Soc. 119 1997 3205 3211
31. R. Acharya, M. Gupta, S. Ramakumar, U.A. Ramagopal, and V.S. Chauhan BMC Struct. Biol. 2007 7
32. Y. Inai, K. Tagawa, A. Takasu, T. Hirabayashi, T. Oshikawa, and M. Yamashita J. Am. Chem. Soc. 122 2000 11731 11732
33. U.A. Ramagopal, S. Ramakumar, P. Mathur, R.M. Joshi, and V.S. Chauchan Prot. Eng. 15 2002 331 335
34. E. Gross, and J.L. Morell J. Am. Chem. Soc. 89 1967 2891 2892
35. W.C. Chan, M. Leyland, J. Clark, H.M. Dodd, L.-Y. Lian, M.J. Gasson, B.W. Bycroft, and G.C.K. Roberts FEBS Lett. 390 1996 133 136
36. R. Donovick, J.F. Pagano, H.A. Stout, and M.J. Weinstein Antibiot. Ann. 3 1955 554 559
37. G.H. Fishera, P. Berryera, J.W. Ryana, V.S. Chauchan, and C.H. Stammer Arch. Biochem. Biophys. 211 1981 269 275
38. A. Lombardi, B. D'Agostino, A. Filippelli, C. Pedone, M.G. Matera, M. Falciani, M. De Rosa, F. Rossi, and V. Pavone Bioorg. Med. Chem. Lett. 8 1998 1153 1156
39. Z. Shimohigashi, H. Kodama, S. Imazu, H. Horimoto, K. Sakaguchi, M. Waki, H. Uchida, M. Kondo, T. Kato, and N. Izumiya FEBS Lett. 222 1987 251 255
40. G. Lentzen, R. Klinck, N. Matassova, F. Aboul-ela, and a.I. Murchie Chem. Biol. 10 2003 769 778
41. H.A. Grigoryan, A.A. Hambardzumyan, M.V. Mkrtchyan, V.O. Topuzyan, G.P. Halebyan, and R.S. Asatryan Chem. Biol. Interact. 171 2008 108 116
42. H.I. Mosberg, R.K. Dua, I.D. Pogozheva, and A.L. Lomize Biopolymers 39 1996 287 296
43. M.B.R. Makowski, Z. Kubica, and P. Wieczorek Liebigs Ann. Chem. 1984 920 928
44. M.B.R. Makowski, Z. Kubica, and G. Pietrzynski Liebigs Ann. Chem. 1985 893 900
45. T.D. Goddard, D.G. Kneller, University of California, San Francisco.
46. E. Ammalahti, M. Bardet, D. Molko, and J. Cadet J. Magn. Res. A 122 1996 230
47. C.D. Schwieters, J.J. Kuszewski, N. Tjandra, and G.M. Clore J. Magn. Res. 160 2003 66 74
48. N. Sewald, and H.D. Jakubke Peptides: Chemistry and Biology 2002 Wiley-VCH Verlag GmbH & Co KGaA
49. B. Miehlich, A. Savin, H. Stoll, and H. Preuss Chem. Phys. Lett. 157 1989 200 206
50. A.D. Becke Phys. Rev. A 38 1988 3098 3100
51. V.A. Rassolov, M.A. Ratner, J.A. Pople, P.C. Redfern, and L.A. Curtiss J. Comp. Chem. 22 2001 976 984
52. J. Tomasi, B. Mennucci, and R. Cammi Chem. Rev. 105 2005 2999 3093
53. 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.J.A. Montgomery, 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, 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, Wallingford, CT, 2009.
54. R.S. Ramakumar, U.A. Ramagopal, Y. Inai, S. Goel, D. Sahal, and V.S. Chauchan Structure 12 2004 389 396
55. M. Gupta, S. Ramakumar, and V.S. Chauhan Biopolymers 80 2005 617 627
56. A. Gupta, A. Bharadwaj, and V.S. Chauhan J. Chem. Soc., Perkin Trans. 2 11 1990 1911 1916
57. A. Bharadwaj, A. Jaswal, and V.S. Chauhan Tetrahedron 48 1992 2691 2708
58. M. Lisowski, Jaremko, M. Jaremko, A. Mazur, R. Latajka, and M. Makowski Biopolymers 93 2010 1055 1064
59. T. Cierpicki, I. Zhukov, R.A. Byrd, and J.J. Otlewski Magn. Reson. 157 2002 178 180
60. R. Latajka, M. Makowski, M. Jewginski, M. Pawelczak, H. Koroniak, and P. Kafarski New J. Chem. 30 2006 1009 1018
61. G. Green, and E. Shaw J. Biol. Chem. 256 1981 1923 1928