First homo-peptides undergoing a reversible 310-helix/ α-helix transition: Critical main-chain length

Biopolymers - Peptide Science Section

Volumn 90, Issue 4, 2008, Pages 567-574

  Moretto, Alessandro ^a   Formaggio, Fernando ^a   Kaptein, Bernard ^b   Broxterman, Quirinus B ^b   Wu, Ling ^c   Keiderling, Timothy A ^c   Toniolo, Claudio ^a  

^a UNIVERSITY OF PADOVA   (Italy)

^b Catalysis and Development   (Netherlands)

^c UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

Author keywords

C tetrasubstituted amino acid; Electronic circular dichroism; Helix to helix transition; Peptide helices; Vibrational circular dichroism

Indexed keywords

ELECTRONIC CIRCULAR DICHROISM; HELIX-TO-HELIX TRANSITION; PEPTIDE HELICES; VIBRATIONAL CIRCULAR DICHROISM;

AMINES;

ACETAMIDE; ACETYL ALPHA METHYLVALYL ALPHA METHYLVALYL ALPHA METHYLVALYL ALPHA METHYLVALYL ALPHA METHYLVALINE; ACETYL ALPHA METHYLVALYL ALPHA METHYLVALYL ALPHA METHYLVALYL ALPHA METHYLVALYL ALPHA METHYLVALINE METHYL ESTER; ACETYL ALPHA METHYLVALYL ALPHA METHYLVALYL ALPHA METHYLVALYL ALPHA METHYLVALYL ALPHA METHYLVALINE TERT BUTYL ESTER; ACETYL ALPHA METHYLVALYL ALPHA METHYLVALYL ALPHA METHYLVALYL ALPHA METHYLVALYL ALPHA METHYLVALYL ALPHA METHYLVALINE; ACETYL ALPHA METHYLVALYL ALPHA METHYLVALYL ALPHA METHYLVALYL ALPHA METHYLVALYL ALPHA METHYLVALYL ALPHA METHYLVALINE METHYL ESTER; ACETYL ALPHA METHYLVALYL ALPHA METHYLVALYL ALPHA METHYLVALYL ALPHA METHYLVALYL ALPHA METHYLVALYL ALPHA METHYLVALYL ALPHA METHYLVALINE; ACETYL ALPHA METHYLVALYL ALPHA METHYLVALYL ALPHA METHYLVALYL ALPHA METHYLVALYL ALPHA METHYLVALYL ALPHA METHYLVALYL ALPHA METHYLVALINE METHYL ESTER; ACETYL ALPHA METHYLVALYL ALPHA METHYLVALYL ALPHA METHYLVALYL ALPHA METHYLVALYL ALPHA METHYLVALYL ALPHA METHYLVALYL ALPHA METHYLVALINE TERT BUTYL ESTER; ACETYL ALPHA METHYLVALYL ALPHA METHYLVALYL ALPHA METHYLVALYL ALPHA METHYLVALYL ALPHA METHYLVALYL ALPHA METHYLVALYL ALPHA METHYLVALYL ALPHA METHYLVALINE METHYL ESTER; ACETYL ALPHA METHYLVALYL ALPHA METHYLVALYL ALPHA METHYLVALYL ALPHA METHYLVALYL ALPHA METHYLVALYL ALPHA METHYLVALYL ALPHA METHYLVALYLISOPROPYLAMIDE; BENZOYLOXYCARBONYL ALPHA METHYLVALYL ALPHA METHYLVALYL ALPHA METHYLVALYL ALPHA METHYLVALYL ALPHA METHYLVALYL ALPHA METHYLVALYL ALPHA METHYLVALYLISOPROPYLAMIDE; METHANOL; OLIGOMER; PEPTIDE; TRIFLUOROACETIC ACID; UNCLASSIFIED DRUG; URETHAN;

ALPHA HELIX; AMINO ACID SEQUENCE; AMINO ACID SUBSTITUTION; AMINO TERMINAL SEQUENCE; ARTICLE; CARBOXY TERMINAL SEQUENCE; CIRCULAR DICHROISM; CONFORMATIONAL TRANSITION; ELECTRONIC CIRCULAR DICHROISM; PROTEIN SYNTHESIS; SEQUENCE ANALYSIS; SOLVATION; VIBRATIONAL CIRCULAR DICHROISM;

CIRCULAR DICHROISM; PEPTIDES; PROPANOLS; PROTEIN STRUCTURE, SECONDARY; SOLUTIONS; SPECTROSCOPY, FOURIER TRANSFORM INFRARED;

EID: 52949120662     PISSN: 00063525     EISSN: 10970282     Source Type: Journal    
DOI: 10.1002/bip.21016     Document Type: Article

References (71)

1. Toniolo, C.; Benedetti, E. Trends Biochem Sci 1991, 16, 350-353.
2. Millhauser, G. L. Biochemistry 1995, 34, 3873-3877.
3. Bolin, K. A.; Millhauser, G. L. Acc Chem Res 1999, 32, 1027-1033.
4. Tanaka, M. Chem Pharm Bull 2007, 55, 349-358.
5. Barlow, D. J.; Thornton, J. M. J Mol Biol 1988, 201, 601-619.
6. Nagaraj, R.; Balaram, P. Acc Chem Res 1981, 14, 356-362.
7. Toniolo, C.; Peggion, C.; Crisma, M.; Formaggio, F.; Shui, X.; Eggleston, D. S. Nat Struct Biol 1994, 1, 908-914.
8. Toniolo, C.; Crisma, M.; Formaggio, F.; Peggion, C.; Epand, R. F.; Epand, R. M. Cell Mol Life Sci 2001, 58, 1179-1188.
9. Peggion, C.; Formaggio, F.; Crisma, M.; Epand, R. F.; Epand, R.M.; Toniolo, C. J Pept Sci 2003, 9, 679-689.
10. Crisma, M.; Peggion, C.; Baldini, C.; Mac Lean, E. J.; Vedovato, N.; Rispoli, G.; Toniolo, C. Angew Chem Int Ed Engl 2007, 46, 2047-2050.
11. Karle, I. L.; Balaram, P. Biochemistry 1990, 29, 6747-6756.
12. Karle, I. L. Acc Chem Res 1999, 32, 693-701.
13. Toniolo, C.; Crisma, M.; Formaggio, F.; Peggion, C. Biopolymers (Pept Sci) 2001, 60, 396-419.
14. Pavone, V.; Gaeta, G.; Lombardi, A.; Nastri, F.; Maglio, O.; Isernia, C.; Saviano, M. Biopolymers 1996, 38, 705-721.
15. Venkatachalam, C. M. Biopolymers 1968, 6, 1425-1436.
16. Toniolo, C.; Crisma, M.; Formaggio, F.; Peggion, C; Broxterman, Q. B.; Kaptein, B. Biopolymers (Pept Sci) 2004, 76, 162-176.
17. Prakash, B.; Praefcke, G. J. K.; Renault, L.; Wittinghofer, A.; Herrmann, C. Nature 2000, 403, 567-570.
18. Koronakis, V.; Sharff, A.; Koronakis, E.; Luisi, B.; Hughes, C. Nature 2000, 405, 914-918.
19. Junop, M. S.; Modesti, M.; Guarné, A.; Ghirlanda, R.; Gellert, M.; Yang, W. EMBO J 2000, 19, 5962-5970.
20. Buchanan, S. K. Trends Biochem Sci 2001, 26, 3-5.
21. Falke, J. J.; Hazelbauer, G. L. Trends Biochem Sci 2001, 26, 257-264.
22. MacKenzie, K. R. Chem Rev 2006, 106, 1931-1977.
23. Pavone, V.; Di Blasio, B.; Santini, A.; Benedetti, E.; Pedone, C.; Toniolo, C.; Crisma, M. J Mol Biol 1990, 214, 633-635.
24. Toniolo, C.; Crisma, M.; Bonora, G. M.; Benedetti, E.; Di Blasio, B.; Pavone, V.; Pedone, C.; Santini, A. Biopolymers 1991, 31, 129-138.
25. Gessmann, R.; Brückner, H.; Petratos, K. J Pept Sci 2003, 9, 753-762.
26. Goodman, M.; Verdini, A. S.; Toniolo, C.; Phillips, W. P.; Bovey, F. A. Proc Natl Acad Sci USA 1969, 64, 444-450.
27. Benedetti, E.; Bavoso, A.; Di Blasio, B.; Pavone, V.; Pedone, C.; Crisma, M.; Bonora, G. M.; Toniolo, C. J Am Chem Soc 1982, 104, 2437-2444.
28. Toniolo, C.; Bonora, G. M.; Barone, V.; Bavoso, A.; Benedetti, E.; Di Blasio, B.; Grimaldi, P.; Lelj, F.; Pavone, V.; Pedone, C. Macromolecules 1985, 18, 895-902.
29. Tirado-Rives, J.; Jorgensen, W. L. Biochemistry 1991, 30, 3864-3871.
30. Soman, K. V.; Karaimi, A.; Case, D. A. Biopolymers 1991, 31, 1351-1361.
31. Huston, S. E.; Marshall, G. R. Biopolymers 1994, 34, 75-90.
32. Sheinerman, F. B.; Brooks, C. L., III. J Am Chem Soc 1995, 117, 10098-10103.
33. Rohl, C. A.; Doig, A. J. Protein Sci 1996, 5, 1687-1696.
34. Donald, F.; Hungerford, G.; Birch, D. J. S.; Moore, B. D. J Chem Soc Chem Commun 1995, 313-314.
35. Hungerford, G.; Martinez-Insua, M.; Birch, D. J. S.; Moore, B. D. Angew Chem Int Ed Engl 1996, 35, 326-329.
36. Pengo, P.; Pasquato, L.; Moro, S.; Brigo, A.; Fogolari, F.; Broxterman, Q. B.; Kaptein, B.; Scrimin, P. Angew Chem Int Ed Engl 2003, 42, 3388-3392.
37. Bellanda, M.; Mammi, S.; Geremia, S.; Demitri, N.; Randaccio, L.; Broxterman, Q. B.; Kaptein, B.; Pengo, P.; Pasquato, L.; Scrimin, P. Chem - Eur J 2007, 13, 407-416.
38. Yoder, G.; Polese, A.; Silva, R. A. G. D.; Formaggio, F.; Crisma, M.; Broxterman, Q. B.; Kamphuis, J.; Toniolo, C.; Keiderling, T. A. J Am Chem Soc 1997, 119, 10278-10285.
39. Mammi, S.; Rainaldi, M.; Bellanda, S.; Schievano, E.; Peggion, E.; Broxterman, Q. B.; Formaggio, F.; Crisma, M.; Toniolo, C. J Am Chem Soc 2000, 122, 11735-11736.
40. Maekawa, H.; Toniolo, C.; Moretto, A.; Broxterman, Q. B.; Ge, N.-H. J Phys Chem B 2006, 110, 5834-5837.
41. Maekawa, H.; Toniolo, C.; Broxterman, Q. B.; Ge, N.-H. J Phys Chem B 2007, 111, 3222-3235.
42. Middleton, W. J.; Lindsey, R. V., Jr. J Am Chem Soc 1964, 86, 4948-4952.
43. Polese, A.; Formaggio, F.; Crisma, M.; Valle, G.; Toniolo, C.; Bonora, G. M.; Broxterman, Q. B.; Kamphuis, J. Chem - Eur J 1996, 2, 1104-1111.
44. Toniolo, C.; Bonora, G. M.; Fontana, A. Int J Pept Protein Res 1974, 6, 371-380.
45. Baron, M. H.; de Lozé, C.; Toniolo, C.; Fasman, G. D. Biopolymers 1978, 17, 2225-2239.
46. Toniolo, C.; Bonora, G. M.; Mutter, M. J Am Chem Soc 1979, 101, 450-454.
47. Moretto, A.; Crisma, M.; Formaggio, F.; Kaptein, B.; Broxterman, Q. B.; Keiderling, T. A.; Toniolo, C. Biopolymers (Pept Sci) 2007, 88, 233-238.
48. Crisma, M.; Saviano, M.; Moretto, A.; Broxterman, Q. B.; Kaptein, B.; Toniolo, C. J Am Chem Soc 2007, 129, 15471-15473.
49. Moretto, A.; Crisma, M.; Formaggio, F.; Toniolo, C.; Wu, L.; Keiderling, T. A.; Kaptein, B.; Broxterman, Q. B. In Peptides for Youth; Escher, E.; Lubell, W. D.; Del Valle S., Eds.; Springer: Secaucus, NJ, in press.
50. Tanaka, M.; Demizu, Y.; Doi, M.; Kurihara, M.; Suemune, H. Angew Chem Int Ed Engl 2004, 43, 5360-5363.
51. Crisma, M.; Moretto, A.; Rainaldi, M.; Formaggio, F.; Broxterman, Q. B.; Kaptein, B.; Toniolo, C. J Pept Sci 2003, 9, 620-637.
52. Keiderling, T. A.; Kubelka, J.; Hilario, J. In Vibrational Spectroscopy of Polymers and Biological Systems; Braiman, M.; Gregoriou, V., Eds.; Taylor and Francis: Atlanta, GA, 2006; pp 253-324.
53. Toniolo, C.; Polese, A.; Formaggio, F.; Crisma, M.; Kamphuis, J. J Am Chem Soc 1996, 118, 2744-2745.
54. Toniolo, C.; Formaggio, F.; Tognon, S.; Broxterman, Q. B.; Kaptein, B.; Huang, R.; Setnicka, V.; Keiderling, T. A.; McColl, I. H.; Hecht, L.; Barron, L. D. Biopolymers 2004, 75, 32-45.
55. Beychok, S. In Poly-α-Amino Acids: Protein Models for Conformational Studies; Fasman, G. D., Ed.; Dekker: New York, 1967; pp 293-337.
56. Hong, D.-P.; Hoshino, M.; Kuboi, R.; Goto, Y. J Am Chem Soc 1999, 121, 8427-8433.
57. Kubasik, M.; Blom, A. Chembiochem 2005, 6, 1187-1190.
58. Yasui, S. C.; Keiderling, T. A.; Bonora, G. M.; Toniolo, C. Biopolymers 1986, 25, 79-89.
59. Yasui, S. C.; Keiderling, T. A.; Formaggio, F.; Bonora, G. M.; Toniolo, C. J Am Chem Soc 1986, 108, 4988-4993.
60. Silva, R. A. G. D.; Yasui, S. C.; Kubelka, J.; Formaggio, F.; Crisma, M.; Toniolo, C.; Keiderling, T. A. Biopolymers 2002, 65, 229-243.
61. Miyazawa, T. In Poly-α-Amino Acids: Protein Models for Conformational Studies; Fasman, G. D., Ed.; Dekker: New York, 1967; pp 69-103.
62. Kennedy, D. F.; Crisma, M.; Toniolo, C.; Chapman, D. Biochemistry 1991, 30, 6541-6548.
63. Kubelka, J.; Silva, R. A. G. D.; Keiderling, T. A. J Am Chem Soc 2002, 124, 5325-5332.
64. Ha, S.-W.; Asakura, T.; Kishore, R. Biomacromolecules 2006, 7, 18-23.
65. Bavoso, A.; Benedetti, E.; Di Blasio, B.; Pavone, V.; Pedone, C.; Toniolo, C.; Bonora, G. M. Proc Natl Acad Sci USA 1986, 83, 1988-1992.
66. Marshall, G. R.; Hodgkin, E. E.; Langs, D. A.; Smith, G. D.; Zabrocki, J.; Leplawy, M. T. Proc Natl Acad Sci USA 1990, 87, 487-491.
67. Pavone, V.; Benedetti, E.; Di Blasio, B.; Pedone, C.; Santini, A.; Bavoso, A.; Toniolo, C.; Crisma, M.; Sartore, L. J Biomol Struct Dyn 1990, 7, 1321-1331.
68. Benedetti, E.; Di Blasio, B.; Pavone, V.; Pedone, C.; Santini, A.; Bavoso, A.; Toniolo, C.; Crisma, M.; Sartore, L. J Chem Soc, Perkin Trans 2, 1990, 1829-1837.
69. Jaun, B.; Tanaka, M.; Seiler, P.; Kühnle, F. N. M.; Braun, C.; Seebach, D. Liebigs Ann 1997, 1697-1710.
70. Formaggio, F.; Crisma, M.; Bonora, G. M.; Pantano, M.; Valle, G.; Toniolo, C.; Aubry, A.; Bayeul, D.; Kamphuis, J. Pept Res 1995, 8, 6-15.
71. Formaggio, F.; Crisma, M.; Toniolo, C.; Broxterman, Q. B.; Kaptein, B.; Corbier, C.; Saviano, M.; Palladino, P.; Benedetti, E. Macromolecules 2003, 36, 8164-8170.