Switching of turn conformation in an aspartate anion peptide fragment by NH ⋯ O- hydrogen bonds

Biopolymers - Peptide Science Section

Volumn 80, Issue 2-3, 2005, Pages 233-248

  Onoda, Akira ^a   Yamamoto, Hitoshi ^a   Yamada, Yusuke ^a   Lee, Keonil ^a   Adachi, Seiji ^a   Okamura, Taka Aki ^a   Yoshizawa Kumagaye, Kumiko ^b   Nakajima, Kiichiro ^b   Kawakami, Toru ^a   Aimoto, Saburo ^a   Ueyama, Norikazu ^a  

^a OSAKA UNIVERSITY   (Japan)

^b Peptide Institute   (Japan)

Author keywords

Aspartate anion; Aspartic acid protease model peptides; Conserved amino acid fragments; Deprotonation; Hairpin turn; Hydrogen bonds; Protonation; Turn conformation

Indexed keywords

CARBOXYLIC ACIDS; CONFORMATIONS; HYDROGEN BONDS; INFRARED SPECTROSCOPY; MICELLES; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYETHERS; SYNTHESIS (CHEMICAL);

ASPARTIC ACID; DEPROTONATION; INTRAMOLECULAR HYDROGEN BONDS; PROTONATION;

PROTEINS;

ACETONITRILE; ALANINE; AMINE; ANION; ASPARTIC ACID; ASPARTIC PROTEINASE; CARBOXYLIC ACID; GLYCINE; MACROGOL DERIVATIVE; MACROGOL LAURYL ETHER; OXYGEN; PEPTIDE; SERINE; UNCLASSIFIED DRUG;

AMINO ACID SEQUENCE; ARTICLE; BETA SHEET; CIRCULAR DICHROISM; CONFORMATIONAL TRANSITION; GENETIC CONSERVATION; HYDROGEN BOND; INFRARED SPECTROSCOPY; MICELLE; PEPTIDE SYNTHESIS; PKA; PROTEIN STABILITY; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT;

AMINO ACID SEQUENCE; ANIONS; ASPARTIC ACID; CIRCULAR DICHROISM; HYDROGEN BONDING; HYDROGEN-ION CONCENTRATION; MODELS, MOLECULAR; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; OLIGOPEPTIDES; PEPTIDE FRAGMENTS; PROTEIN CONFORMATION;

EID: 20344376413     PISSN: 00063525     EISSN: None     Source Type: Journal    
DOI: 10.1002/bip.20187     Document Type: Article

References (38)

1. Haque, T. S.; Little, J. C.; Gellman, S. H. J Am Chem Soc 1994, 116, 4105-4016.
2. Haque, T. S.; Little, J. C.; Gellman, S. H. J Am Chem Soc 1996, 118, 6975-6985.
3. Stanger, H. E.; Gellman, S. H. J Am Chem Soc 1998, 120, 4236-4237.
4. Sharman, G. J.; Searle, M. S. J Am Chem Soc 1998, 120, 4869-4870.
5. Haung, F.; Nau, W. M. Angew Chem Int Ed 2003, 42, 2269-2272.
6. Kotler, M.; Katz, R.; Skalka, A. M. J Virol 1988, 62, 2696-2700.
7. Le Grice, S. F.; Mills, J.; Mous, J. EMBO J 1988, 7, 2547-2556.
8. Kohl, N. E.; Emini, E. A.; Schleif, W. A.; Davis, L. J.; Heimbach, J. C.; Dixon, R. A.; Scolnick, E. M.; Sigal, I. S. Proc Natl Acad Sci USA 1988, 85, 4686-4690.
9. Loeb, D. D.; Hutchison, C. A., III; E., M. H.; Farmerie, W. G.; Swanstrom, R. J Virol 1989, 63, 111-121.
10. Mous, J.; Heimer, E. P.; Le Grice, S. F. J Virol 1988, 62, 1433-1436.
11. Veerapandian, B.; Cooper, J. B.; Šali, A.; Blundel, T. L.; Rosati, R. L.; Dominy, B. W.; Damon, D. B.; Hoover, D. J. Protein Sci 1992, 1, 322-328.
12. Coates, L.; Erskine, P. T.; Wood, S. P.; Myles, D. A. A.; Cooper, J. B. Biochemistry 2001, 40, 13149-13157.
13. Suguna, K.; Bott, R. R.; Padlan, E. A.; Subramanian, E.; Sheriff, S.; Cohen, G. H.; Davies, D. R. J Mol Biol 1987, 196, 877-900.
14. Suguna, K.; Padlan, E. A.; Smith, C. W.; Carlson, D. W.; Davies, D. R. Proc Natl Acad Sci USA 1987, 84, 7009-7013.
15. Fujinaga, M.; Chernaia, M. M.; Tarosova, N. I.; Mosimann, S. C.; James, M. N. G. Protein Sci 1995, 4, 960-972.
16. Wlodawer, A.; Millar, M.; Jaskólski, M.; Sathyanarayana, B. K.; Baldwin, E.; Weber, I. T.; Selk, L. M.; Clawson, L.; Schneider, J.; Kent, S. B. H. Science 1989, 245, 616-621.
17. Cruikahank, D. P.; Hartmann, W. K.; Tholen, D. J. Nature 1985, 315, 122-124.
18. Millar, M.; Jaskólski, M.; Mohano Rao, J. K.; Leis, J.; Wlodawer, A. Nature 1989, 337, 576-579.
19. Onoda, A.; Yamada, Y.; Takeda, J.; Okamura, T.; Doi, M.; Yamamoto, H.; Ueyama, N. Bull Chem Soc Jpn 2004, 77, 321-329.
20. Onoda, A.; Yamada, Y.; Nakayama, Y.; Takahashi, K.; Adachi, H.; Okamura, T.; Nakamura, A.; Yamamoto, H.; Ueyama, N.; Vyprachticky, D.; Okamoto, Y. Inorg Chem 2004, 43, 4447-4455.
21. Onoda, A.; Yamada, Y.; Okamura, T.; Doi, M.; Yamamoto, H.; Ueyama, N. J Am Chem Soc 2002, 124, 1052-1059.
22. Onoda, A.; Yamada, Y.; Doi, M.; Okamura, T.; Ueyama, N. Inorg Chem 2001, 516-521.
23. Onoda, A. Inorg Chem 2002, 41, 6038-6047.
24. Ueyama, N.; Hosoi, T.; Yamada, Y.; Doi, M.; Okamura, T.; Nakamura, A. Macromolecules 1998, 31, 7119-7126.
25. Ueyama, N.; Takeda, J.; Yamada, Y.; Onoda, A.; Okamura, T.; Nakamura, A. Inorg Chem 1999, 38, 475-478.
26. Ueyama, N.; Kozuki, H.; Doi, M.; Yamada, Y.; Takahashi, K.; Onoda, A.; Okamura, T.; Yamamoto, H. Macromolecules 2001, 34, 2607-2614.
27. Takahashi, K.; Doi, M.; Kobayashi, A.; Tagushi, T.; Onoda, A.; Okamura, T.; Yamamoto, H.; Ueyama, N. Chem Lett 2004, 33, 192-193.
28. Joshi, H. V.; Meier, M. S. J Am Chem Soc 1996, 118, 12038-12044.
29. James, M. N. G.; Sielecki, A. R.; Hayamakawa, K.; Gelb, M. H. Biochemistry 1992, 31, 3872-3886.
30. Silva, A. M.; Cachau, R. E.; Cham, H. L.; Erickson, J. W. J Mol Biol 1996, 255, 324-346.
31. Park, H.; Suh, J.; Lee, S. J Am Chem Soc 2000, 122, 3901-3908.
32. Bax, A.; Davis, D. G. J Magn Reson 1985, 65, 355-360.
33. Braunschweiler, L.; Ernst, R. R. J Magn Reson 1983, 53, 521-528.
34. Bothner-By, A. A.; Stephens, R. L.; Lee, J.-M.; Warren, C. D.; Jeanloz, R. W. J Am Chem Soc 1984, 106, 577-564.
35. Rance, M. J. J Magn Reson 987, 74, 557-564.
36. Chang, D. K.; Cheng, S. F.; Trivedi, V. D. J Biol Chem 1999, 274, 5299-5309.
37. Chang, D. K.; Cheng, S. F.; Trivedi, V. D.; Yang, S. H. J Biol Chem 1999, 275, 19150-19158.
38. Lindberg, M.; Jarvet, J.; Langel, U.; Graeslund, A. Biochemistry 2001, 40, 3141-3149.