Analysis of the conformational profile of trishomocubane amino acid dipeptide

Biopolymers

Volumn 81, Issue 5, 2006, Pages 339-349

  Bisetty, Krishna ^a   Govender, Penny ^b   Kruger, Hendrik G ^c  

^a DURBAN UNIVERSITY OF TECHNOLOGY   (South Africa)

^b UNIVERSITY OF JOHANNESBURG   (South Africa)

^c UNIVERSITY OF KWAZULU NATAL   (South Africa)

Author keywords

Ab initio; AMBER (parm94); Cage dipeptide; Conformational study; Molecular mechanics; Trishomocubane; Unnatural amino acids

Indexed keywords

ACETYLATION; BIOPOLYMERS; CARBOXYLATION; CONFORMATIONS; POLYPEPTIDES; PROTEINS;

AB INITIO; AMBER (PARM94); CAGE DIPEPTIDES; CONFORMATIONAL STUDY; MOLECULAR MECHANICS; TRISHOMOCUBANE; UNNATURAL AMINO ACIDS;

AMINO ACIDS;

4 AMINO (D3) TRISHOMOCUBANE 4 CARBOXYLIC ACID; ALPHA AMINO ACID; AMINO ACID; CARBOXYLIC ACID DERIVATIVE; DIPEPTIDE; UNCLASSIFIED DRUG;

ARTICLE; CARBOXY TERMINAL SEQUENCE; MOLECULAR MECHANICS; PROTEIN ANALYSIS; PROTEIN CONFORMATION; PROTEIN STRUCTURE;

AMINO ACIDS; BIOPOLYMERS; BRIDGED COMPOUNDS; CARBON; DIPEPTIDES; ELECTROSTATICS; HYDROGEN BONDING; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, CHEMICAL; MODELS, MOLECULAR; MODELS, THEORETICAL; MOLECULAR CONFORMATION; PROTEIN STRUCTURE, TERTIARY; SOFTWARE; X-RAY DIFFRACTION;

EID: 33645690366     PISSN: 00063525     EISSN: 10970282     Source Type: Journal    
DOI: 10.1002/bip.20423     Document Type: Article

References (35)

1. Noren, C. J.; Anthoney-Cahill, S. J.; Griffith, M. C.; Schultz, P. G. Science 1989, 224, 182-188.
2. Roesser, J. R.; Chorghade, M. S.; Hecht, S. M. Biochemistry 1986, 25, 6361-6365.
3. Hanessian, S.; McNaughton-Smith, G.; Lombart, H. G.; Lubell, W. D. Tetrahedron 1997, 53, 12789-12854.
4. Brookes, K. B.; Hickmott, P. W.; Jutle, K. K.; Schreyer, C. A. S Afr J Chem 1992, 45, 8-11.
5. Oliver, D. W.; Dekker, D. G.; Snykers, F. O. Eur J Med Chem 1991, 26, 375-379.
6. Oliver, D. W.; Dekker, D. G.; Snykers, F. O. J Med Chem 1991, 34, 851-854.
7. Geldenhuys, W. J.; Malan, S. F.; Bloomquist, J. R.; Marchand, A. P.; Van der Schyf, C. J. Med Res Rev 2005, 25, 21-48.
8. Govender, T.; Kruger, H. G.; Raasch, T. Struct Chem 2005, 16, 129-134.
9. Govender, T.; Hariprakasha, H. K.; Kruger, H. G.; Raasch, T. S Afr J Chem 2005, 58, 37-40.
10. Jimenez, A. I.; Cativiela, C.; Aubry, A.; Marraud, M.; J Am Chem Soc 1998, 120, 9452-9459.
11. Wilkes, B. C.; Schiller, P. W. Biopolymers 1994, 34, 1213-1219.
12. Thurieau, C.; Feletou, M.; Hennig, P.; Raimbaud, E.; Canet, E.; Fauchere, J. L. J Med Chem 1996, 39, 2095-2101.
13. Vitoux, B.; Aubry, A.; Cung, M. T.; Marraud, M. Int J Pept Protein Res, 1986, 27, 617-632.
14. Bisetty, K.A Computational Study of Cage Peptides; Ph.D. thesis; University of Natal, Durban, 2002.
15. Bisetty, K.; Gomez-Catalan, J.; Aleman, C.; Giralt, E.; Kruger, H. G.; Perez, J. J. J Pept Sci 2004, 10, 274-284.
16. Bisetty, K.; Catalan, J. G.; Kruger, H. G.; Perez, J. J. J Mol Struct (Theochem) 2005, 731, 127-137.
17. Möhle, K.; Gubmann, M.; Hofmann, H.-J. J Comp Chem 1997, 18, 1415-1430.
18. Rose, G. D.; Gierasch, L. M.; Smith, J. A. Adv Protein Chem 1985, 37, 1-109.
19. Venkatachalam, C. M. Biopolymers, 1968, 6, 1425-1436.
20. Axt, M.; Oulyadi, H.; Pannecoucke, X.; Quirion, J. C.; Pohlmann, A. R.; Costa, V. E. U. J Mol Struct 2004, 689, 49-60.
21. Oliver, D. W.; Dekker, D. G. (D3)-Trishomocubane stereoisomerism, S Afr J Chem 1988, 84, 407-409.
22. Nakazaki, M.; Naemura, K.; Arashiba, N. J Org Chem, 1978, 43, 689-692.
23. Kent, G. J.; Godleski, S. A.; Õsawa, E.; Schleyer, P. R. J Org Chem 1977, 42, 3852-3859.
24. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, Jr., J. A.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C. Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A. Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K. Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, Revision A. 3; Gaussian Inc.: Pittsburgh, PA, 1998.
25. Case, D. A.; Pearlman, D. A.; Caldwell, J. W.; Cheatham III, T. E.; Ross, W. S.; Simmerling, C. L.; Darden, T. A.; Merz, K. M.; Stanton, R. V.; Cheng, A. L.; Vincent, J. J.; Crowley, M.; Ferguson, D. M.; Radmer, R. J.; Seibel, G. L.; Singh, U. C.; Weiner, P. K.; Pearlman, D. A.; Kollman, P. A. AMBER 5.0; University of California: San Francisco, 1997.
26. Weiner, S. J.; Kollman, P. A.; Case, D. A.; Singh, U. C.; Ghio, C.; Alagona, G.; Profeta, S., Jr.; Weiner, P. J. J Am Chem Soc 1984, 106, 765-784.
27. Cornell, W. D.; Cieplak, P.; Bayly, C. L.; Gould, I. R.; Merz, K. M.; Ferguson, D. M.; Spellmeyer, D. C.; Fox, T.; Caldwell, J. W.; Kollman, P. A. J Am Chem Soc 1995, 117, 5179-5197.
28. Head-Gordon, T.; Head-Gordon, M.; Frisch, M. J.; Brooks III, C. L.; Pople, J. A. J Am Chem Soc 1991, 113, 5989-5997.
29. Böhm, H. J.; Brode, S. J Am Chem Soc 1991, 113, 7129-7135.
30. Gould, I. R.; Cornell, W. D.; Hillier, I. H. J Am Chem Soc 1994, 116, 9250-9256.
31. Cornell, W. D.; Gould, I. R.; Kollman, P. A. J Mol Struct (Theochem) 1997, 392, 101-109.
32. Alemán, C. Conformational properties of the alpha-amino acids disubstituted at the alpha-carbon, J Phys Chem 1997, 101, 5046-5050.
33. Alemán, C.; Perez, J. J. Int J Quantum Chem 1993, 47, 231-238.
34. Alemán, C.; Subirana, J. A.; Perez, J. J. Biopolymers 1992, 32, 621-631.
35. Filizola, M.; Centeno, N. B.; Perez, J. J. J Pept Sci 1997, 3, 85-92.