The microwave spectrum, structure, and ring-puckering of the cyclic dipeptide diketopiperazine

Journal of the American Chemical Society

Volumn 122, Issue 24, 2000, Pages 5856-5860

  Bettens, Fiona L ^a   Bettens, Ryan P A ^a   Brown, Ronald D ^a   Godfrey, Peter D ^a  

^a MONASH UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

DIPEPTIDE; PIPERAZINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CONFORMATION; MICROWAVE RADIATION; MOLECULAR MODEL; PROTEIN FOLDING; X RAY CRYSTALLOGRAPHY;

EID: 0034697673     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja000042n     Document Type: Article

References (31)

1. Stewart, D. E.; Sarkar, A.; Wampler, J. E. J. Mol. Biol. 1990, 214, 253-260.
2. Barrett, G. C.; Elmore, D. T. In Amino Acids and Peptides; Cambridge University Press: Cambridge, United Kingdom, 1998; pp 127-128.
3. Gaines, S. M.; Bada, J. L. J Org. Chem. 1988, 53, 2757-2764.
4. Jonsson, M.; Wayner, D. D. M.; Armstrong, D. A.; Yu, D.; Rauk A. J. Chem. Soc., Perkin Trans. 2 1998, 1967-1972.
5. Palacin, S.; Chin, D. N.; Simanek, E. E.; MacDonald, J. C.; Whitesides, G. M.; McBride, M. T.; Palmore, G. T. S. J Am. Chem. Soc. 1997, 119, 11807-11816.
6. Corey, R. B. J Am. Chem. Soc. 1938, 60, 1598-1604.
7. Degeilh, R.; Marsh, R. E. Acta Crystallogr. 1959, 12, 1007-1014.
8. Hirshfeld, F. L. Acta Crystallogr. 1976, A32, 239-244.
9. Dorset, D. L. Acta Crystallogr. 1991, A47, 510-515.
10. Sletten, E. J. Am. Chem. Soc. 1970, 92, 172-177.
11. Karle, I. L.; Ottenheym, H. C.; Witkop, B. J. Am. Chem. Soc. 1974, 96, 539-543
12. Karplus, S.; Lifson, S. Biopolymers 1971, 10, 1973-1982.
13. Chandrasekaran, R.; Lakshminarayana, A. V.; Mohanalaishnan, P.; Ramanchandran, G. N. Biopolymers 1973, 12, 1421-1425.
14. Ajò, D.; Granozzi, G.; di Bello, C. Biopolymers 1977, 16, 707-714.
15. Ciarkowski, J. Biopolymers 1984, 23, 397-407.
16. Bettens, F. L. In Microwave Studies of the Peptide Linkage and Related Systems. Ph.D. Thesis, Monash University, Clayton, Australia, 1992.
17. Hirst, J. D.; Persson, B. J. J. Phys. Chem. A 1998, 102, 7519-7524
18. Dunning, T. H. J. Chem Phys. 1989, 90, 1007-1023.
19. -1.
20. Brown, R. D.; Crofts, J G.; Godfrey, P. D.; McNaughton, D.; Pierlot, A. P. J. Mol. Struct. 1988, 190, 185-193.
21. 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.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; and Pople, J. A. Gaussian 98, revision A.6; Gaussian, Inc.: Pittsburgh, PA, 1998.
22. (a) Histamine: Godfrey, P. D.; Brown, R. D. J. Am. Chem. Soc. 1998, 120, 10724-10732.
23. (b) β-vinylethanol: Crofts, J. G.; Brown, R. D.; Godfrey, P. D. J. Phys. Chem. A 1999, 103, 3629-3635.
24. (c) Oxalic acid: Godfrey, P. D.; Mirabella, M.; Brown, R. D.; J. Phys. Chem. A 2000, accepted for publication.
25. Champion, R.; Godfrey, P. D.; Bettens, F. L. J. Mol. Spectrosc. 1991, 473, 488-495.
26. Cremer, D.; Pople, J. A. J. Am. Chem. Soc. 1975, 97, 1354-1358.
27. Allen, G. In Protein: A Comprehensive Treatise; Allen, G., Ed.; JAI Press Inc.: Greewich, Connecticut, 1997; Vol. 1, pp 99-136.
28. (a) Levine, I. N. In Quantum Chemistry, 5th ed.; Prentice Hall: Upper Saddle River, NJ, 1999: pp 701-702.
29. (b) Halgren, T. A.; Nachbar, R. B. J. Comput. Chem. 1996, 17, 587.
30. (c) Halgren, T. A. J. Comput. Chem. 1999, 20, 720.
31. TITAN, version 1; Wavefunction, Inc.: Irvine, California; Schrödinger Inc., Portland, Oregon, 1999.