High stability of the polyproline II helix in polypeptide bottlebrushes

Chemistry - A European Journal

Volumn 14, Issue 29, 2008, Pages 8939-8946

  Zhang, Afang ^a   Guo, Yifei ^a  

^a ZHENGZHOU UNIVERSITY   (China)

Author keywords

Conformation analysis; Helical structures; Peptides; Polymerization; Proline

Indexed keywords

ABS RESINS; AMINES; CHEMICAL REACTIONS; CONFORMATIONS; DICHROISM; MONOMERS; OPTICAL PROPERTIES; PEPTIDES; PHOTORESISTS; POLYMERIZATION; SOLUTIONS;

ALIPHATIC ALCOHOLS; AQUEOUS SOLUTIONS; AVERAGE DEGREES; CHARGED STATES; CIRCULAR DICHROISMS; CONFORMATION ANALYSIS; CONFORMATIONAL STABILITIES; DIFFERENT SOLVENTS; HELICAL CONFORMATIONS; HELICAL STRUCTURES; HELIX CONTENTS; HIGH STABILITIES; LINEAR POLYMER CHAINS; MONODISPERSE; OLIGOPEPTIDES; PEPTIDE SIDE CHAINS; POLYPROLINE; POLYPROLINE II (PPII); POLYPROLINE II HELIXES; PROLINE; SIDE CHAINS;

POLYMERS;

FREE RADICAL; PEPTIDE; POLYPROLINE;

ARTICLE; CHEMISTRY; CIRCULAR DICHROISM; PROTEIN SECONDARY STRUCTURE;

CIRCULAR DICHROISM; FREE RADICALS; PEPTIDES; PROTEIN STRUCTURE, SECONDARY;

EID: 55049102301     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200801191     Document Type: Article

References (82)

1. a) Y. Okamoto, E. Yashima, C. Yamamoto in Materials-Chirality (Eds.: M. M. Green, R. J. M. Nolte, E. W. Meijer), Wiley, New York, 2003, pp. 157-208;
2. b) J. W. Lockman, N.M. Paul, J. R. Parquette, Prog. Polym. Sci. 2005, 30, 423-452;
3. c) D. B. Amabilino, J. Veciana, Top. Curr. Chem. 2006, 265, 253-302;
4. d) D. A. Leigh, E. M. Pérez, Top. Curr. Chem. 2006, 265, 185-208.
5. a) Y. Okamoto, T. Nakano, Chem. Rev. 1994, 94, 349-372;
6. b) T. Nakano, Y. Okamoto, Chem. Rev. 2001, 101, 4013-4038;
7. c) J. J. L. M. Cornelissen, A. E. Rowan, R. J. M. Nolte, N. A. J. M. Sommerdijk, Chem. Rev. 2001, 101, 4039-4070;
8. d) M. M. Green, K.-S. Cheon, S.-Y. Yang, J.-W. Park, S. Swansburg, W. Liu, Acc. Chem. Res. 2001, 34, 672-680;
9. e) E. Yashima, K. Maeda, T. Nishimura, Chem. Eur. J. 2004, 10, 42-51;
10. f) J. O. Rudick, V. Percec, New J. Chem. 2007, 31, 1083-1096.
11. a) A. R. A. Palmans, E. W. Meijer, Angew. Chem. 2007, 119, 9106-9126;
12. Angew. Chem. Int. Ed. 2007, 46, 8948-8968;
13. b) H.-J. Kim, Y.-B. Lim, M. Lee, J. Polym. Sci. Part A Polym. Chem. 2008, 46, 1925-1935;
14. c) O. A. Hembury, V. V. Borovkov, Y. Inoue, Chem. Rev. 2008, 108, 1-73.
15. E. Yashima, K. Maeda, Macromolecules 2008, 41, 3-12.
16. T. Nakano, Y. Okamoto, Macromol. Rapid Commun. 2000, 21, 603-612.
17. a) J. Bella, M. Eaton, B. Brodsky, H. M. Berman, Science 1994, 266, 75-81;
18. b) S. K. Holmgren, K.M. Taylor, L.E. Bretscher, R.T. Raines, Nature 1998, 392, 666-667;
19. c) A. V. Persikov, J. A. Ramshaw, A. Kirkpatrick, B. Brodsky, Biochemistry 2000, 39, 14960-14967;
20. d) A. V. Persikov, J. A. M. Ramshaw, A. Kirkpatrick, B. Brodsky, J. Am. Chem. Soc. 2003, 125, 11500-11501;
21. e) M. Kohlani, T. C. Jones, J. E. Schneider, M. F. Jarrold, J. Am. Chem. Soc. 2004, 126, 7420-7421;
22. f) M. D. Shoulders, J. A. Hodges, R.T. Raines, J. Am. Chem. Soc. 2006, 128, 8112-8113;
23. g) S. Rele, Y. Song, R. P. Apkarian, Z. Qu, V. P. Conticello, E. L. Chaikof, J. Am. Chem. Soc. 2007, 129, 14780-14787;
24. h) V. Gauba, J.D. Harlgerink, J. Am. Chem. Soc. 2007, 129, 15034-15041;
25. i) F.W. Kotch, I.A. Guzei, R.T. Raines, J. Am. Chem. Soc. 2008, 130, 2952-2953;
26. j) N. Dai, X. J. Wang, F. A. Etzkorn, J. Am. Chem. Soc. 2008, 130, 5396-5397;
27. k) D. Diana, B. Ziaco, G. Colombo, G. Scarabelli, A. Romanelli, C. Pedone, R. Fattorusso, L. D. D'Andréa, Chem. Eur. J. 2008, 14, 4164-4166.
28. a) P.M. Cowan, S. Mcgavin, Nature 1955, 176, 501-503;
29. b) W. Traub, U. Shmueli, Nature 1963, 198, 1165-1166.
30. a) R. Z. Dramer, L. Vitagliano, J. Bella, R. Berisio, L. Mazzarella, B. Brodsky, A. Zagari, H. M. Berman, J. Mol. Biol. 1998, 280, 623-638;
31. b) J. T. Nguyen, C. W. Turck, F. E. Cohen, R. N. Zuckermann, W. A. Lim, Science 1998, 282, 2088-2092;
32. c) Z. Shi, K. Chen, Z. Liu, N. R. Kallenbach, Chem. Rev. 2006, 106, 1877-1897.
33. a) M. P. Williamson, Biochem. J. 1994, 297, 249-260;
34. b) D. S. Daniels, A. Scheparlz, J. Am. Chem. Soc. 2007, 129, 14578-14579.
35. a) J. Kurtz, A. Berger, E. Katchalski, Nature 1956, 178, 1066-1067;
36. b) I. Z. Steinberg, W. F. Harriugton, A. Berger, M. Sela, E. Katchalski, J. Am. Chem. Soc. 1960, 82, 5263-5279;
37. c) J. Engel, G. Schwarz, Angew. Chem. 1970, 82, 468-479;
38. Angew. Chem. Int. Ed. Engl. 1970, 9, 389-400;
39. d) M. Mutter, T. Wöhr, S. Gloria, M. Kellar, Biopolymers 1999, 51, 121-128.
40. a) A. R. Downie, A. A. Randall, Trans. Faraday Soc. 1959, 55, 2132-2140;
41. b) F. Gornick, L. Mandelkern, A. F. Diorio, D. E. Roberts, J. Am. Chem. Soc. 1964, 86, 2549-2555;
42. c) J. Engel, Biopolymers 1966, 4, 945-948.
43. a) C. M. Deber, F. A. Bovey, J. P. Carver, E. R. Blout, J. Am. Chem. Soc. 1970, 92, 6191-6198;
44. b) D. A. Torchia, F. A. Bovey, Macromolecules 1971, 4, 246-251;
45. c) D. E. Dorman, F. A. Bovey, J. Org. Chem. 1973, 35, 2379-2383;
46. d) Y.-Y. Chao, R. Bersohn, Biopolymers 1978, 17, 2761-2767.
47. a) H. Okabayashi, T. Isemura, S. Sakakibara, Biopolymers 1968, 6, 323-330;
48. b) N. Helbecque, M. H. Loucheux-Lefebvre, Int. J. Pept. Protein Res. 1982, 19, 94-101;
49. c) F. Rabanal, M. D. Ludevid, M. Pons, E. Giralt, Biopolymers 1993, 33, 1019-1028;
50. d) R.K. Dukor, T. A. Keiderling, Biospectroscopy 1996, 2, 83-100.
51. J.-C. Horng, R. T. Raines, Protein Sci. 2006, 15, 74-83.
52. M. Kümin, L.-S. Sonntag, H. Wennemers, J. Am. Chem. Soc. 2007, 129, 466-467.
53. S. Kakinoki, Y. Hirano, M. Oka, Polym. Bull. 2005, 53, 109-115.
54. a) M. Y. Ogawa, J. F. Wishart, Z. Young, J. R. Miller, S. S. Isied, J. Phys. Chem. 1993, 97, 11456-11463;
55. b) D. G. McCaffery, C. A. Slate, B. M. Nakhle, Tetrahedron 1995, 51, 9859-9872;
56. c) D. G. McCaffery, D. A. Friesen, E. Danielson, Proc. Natl. Acad. Sci. USA 1996, 93, 8200-8204;
57. d) C. A. Slate, R. A. Binstead, T. J. Meyer, B. W. Erickson, Lett. Pept. Sci. 1999, 6, 61-69;
58. e) D. R. Striplin, S. Y. Reece, D.O. McCaffery, C. G. Wall, D.A. Friesen, B.W. Erickson, T. J. Meyer, J. Am. Chem. Soc. 2004, 126, 5282-5291;
59. f) S. A. Serron, W. Aldridge, C. N. Fleming, R. M. Danell, M. Sykora, M. Baik, D. M. Dattelbaum, T. J. Meyer, J. Am. Chem. Soc. 2004, 126, 14506-14514;
60. g) W. S. Aldridge, B.J. Hornstein, S. Serron, D.M. Dattelbaum, J. R. Schoonover, T.J. Meyer, J. Org. Chem. 2006, 71, 5186-5190.
61. a) L. Crespo, G. Sanclimens, B. Montaner, R. Pérez-Tomás, M. Royo, M. Pons, F. Albericio, E. Giralt, J. Am. Chem. Soc. 2002, 124, 8876-8883;
62. b) G. Sanclimens, L. Crespo, E. Giralt, F. Albericio, M. Royo, J. Org. Chem. 2005, 70, 6274-6281.
63. M. Zhang, A.H.E. Müller, J. Polym. Sci. Part A Polym. Chem. 2005, 43, 461-3481.
64. For polymer bottlebrushes with polydispersed peptide side chains, see, for example: a) B. Zhang, K. Fischer, M. Schmidt, Macromol. Chem. Phys. 2005, 206, 157-162;
65. b) L. Zhang, W. Li, A. Zhang, Prog. Chem. 2006, 18, 939-949;
66. c) T. Waku, M. Matsusaki, T. Kaneko, M. Akashi, Macromolecules 2007, 40, 6385-6392;
67. d) N. Gunari, Y. Cong, B. Zhang, K. Fischer, A. Janshoff, M. Schmidt, Macromol. Rapid Commun. 2008, 29, 821-825.
68. a) A. Zhang, A.D. Schlüter, Chem. Asian J. 2007, 2, 1540-1548;
69. b)A. Zhang, F. Rodríguez-Ropero, D. Zanuy, C. Alemán, E. W. Meijer, A. D. Schlüter, Chem. Eur. J. 2008, 14, 6924-6934.
70. Macromonomer 1 adopts different helical conformations in isopropanol/acetonitrile (1:1) and HFIP, and this difference was expected to indicate different steric effects in the polymerization process. For the corresponding CD spectra of macromonomer 1, see Figure SI in the Supporting Information.
71. A. Zhang, B. Zhang, E. Wächtersbach, M. Schmidt, A. D. Schlüter, Chem. Eur. J. 2003, 9, 6083-6092.
72. HFIP was reported to show effects on polymer-backbone tacticity in radical polymerizations, see, for example: a) Y. Isobe, K. Yamada, T. Nakano, Y. Okamoto, Macromolecules 1999, 32, 5979-5981;
73. b) Y. Isobe, K. Yamada, T. Nakano, Y. Okamoto, J. Polym. Sci. Part A Polym. Chem. 2000, 35, 4693-4703;
74. c) Y. Miura, T. Satoh, A. Narumi, O. Nishizawa, Y. Okamoto, T. Kakuchi, Macromolecules 2005, 35, 1041-1043;
75. d) Y. Miura, T. Satoh, A. Narumi, O. Nishizawa, Y. Okamoto, T. Kakuchi, J. Polym. Sci. Part A Polym. Chem. 2006, 44, 1436-1446.
76. K. Hatada, T. Kitayama, K. Ute, Prog. Polym. Sci. 1988, 13, 189-276.
77. m, is relatively small. We propose that the stable PPII conformation in the present case would only remain for the cylindrical bottlebrushes, in which all of the side chains are aligned in parallel to form the overcrowded structures, For reports regarding bottlebrush shapes, see, for example: a) Y. Tsukahara, K, Tsutsumi, Y. Yamashita, S. Shimada, Macromoleailes 1990, 23, 5201-5208;
78. b) M. Wintermantel, M. Gerle, K. Fischer, M, Schmidt, I. Wataoka, H. Urakawa, K. Kajiwara, Y. Tsukahara, Macromolecules 1996, 29, 978-983;
79. c) P. Dziezok, K. Fischer, M, Schmidt, S. S, Sheiko, M. Möller, Angew. Chem. 1997, 109, 2894-2897;
80. Angew. Chem. Int. Ed. Engl. 1997, 36, 2812-2815;
81. d) K. Fischer, M. Schmidt, Macromol. Rapid Commun. 2001, 22, 787-791;
82. e) S. Rathgeber, T. Pakula, A. Wilk, K. Matyjaszewski, K. L. Beers, J. Chem. Phys. 2005, 122, 124904/1-124904/13.