Conformations and tautomers of 5a, 6-Anhydrotetracycline

Journal of Physical Chemistry B

Volumn 109, Issue 9, 2005, Pages 4279-4284

  Meindl, Kathrin ^a   Clark, Timothy ^a  

^a UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

5A,6-ANHYDROTETRACYCLINE; CONFORMATIONAL EQUILIBRIUM; TETRACYCLINES; TOXIC DEGRADATION; TUATOMERS;

BACTERIA; BROMINE COMPOUNDS; CONFORMATIONS; DEGRADATION; NUCLEAR MAGNETIC RESONANCE; PHOTOLYSIS; PROBABILITY DENSITY FUNCTION; PROTEINS; REGRESSION ANALYSIS; ULTRAVIOLET SPECTROSCOPY; X RAY ANALYSIS;

ANTIBIOTICS;

5A,6-ANHYDROTETRACYCLINE; ANHYDROTETRACYCLINE; TETRACYCLINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; ISOMERISM; SPECTROFLUOROMETRY;

ISOMERISM; MODELS, MOLECULAR; MOLECULAR CONFORMATION; SPECTROMETRY, FLUORESCENCE; TETRACYCLINES;

EID: 15544371290     PISSN: 15206106     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp0451039     Document Type: Article

References (49)

1. (a) Hasan, T.; Allen, M.; Cooperman, B. S. J. Org. Chem. 1985, 50, 1755-1757.
2. (b) Oka, H.; Ikai, Y.; Kawamura, N.; Yamada, M.; Harada, K.; Ito, S.; Suzuki, M. J. Agric. Food Chem. 1989, 37, 226-231.
3. Halling-Sørensen, B.; Sengeløv, G.; Tjørnelund, J. Arch. Environ. Contam. Toxicol. 2002, 42, 263-271.
4. Nelson, M. L. In Tetracyclines in Biology, Chemistry and Medicine; Nelson, M. L., Hillen, W., Greenwald, R. A., Eds.; Birkhäuser Verlag: Basel, Switzerland, 2001; pp 3-63.
5. Scholz, O.; Schubert, P.; Kintrup, M.; Hillen, W. Biochemistry 2000, 39, 10914-10920.
6. Lederer, T.; Kintrup, M.; Takahashi, M.; Sum, P.-E.; Ellestad, G. A.; Hillen, W. Biochemistry 1996, 35, 7439-7446.
7. Saenger, W.; Orth, P.; Kisker, C.; Hillen, W.; Hinrichs, W. Angew. Chem. 2000, 112, 2122-2133.
8. Schnappinger, D.; Hillen, W. Arch. Microbiol. 1996, 165, 359-369.
9. Palenik, G. J.; Mathew, M.; Restivo, R. J. Am. Chem. Soc. 1978, 100, 4458-4464.
10. See, for instance, Casy, A. F.; Yasin, A. Magn. Reson. Chem. 1985, 23, 767-770.
11. See, for instance, (a) Asleson, G. L.; Frank, C. W. J. Am. Chem. Soc. 1975, 97, 6246-6248. (b) Celotti, M.; Fazakerley, G. V. J. Chem. Soc., Perkin Trans. 2, 1977, 1319-1322.
12. See, for instance, (a) Asleson, G. L.; Frank, C. W. J. Am. Chem. Soc. 1975, 97, 6246-6248. (b) Celotti, M.; Fazakerley, G. V. J. Chem. Soc., Perkin Trans. 2, 1977, 1319-1322.
13. (a) Mitscher, L. A.; Bonacci, A. C.; Sokoloski, T. D. Tetrahedron Lett. 1968, 9, 5361-5364.
14. (b) Mitscher, L. A.; Bonacci, A. C.; Sokoloski, T. D. Antimicrob. Agents Chemother. 1968, 8, 78-86.
15. See, for instance, (a) Palenik, G. J.; Bentley, J. A. J. Am. Chem. Soc. 1978, 100, 2863-2867. (b) Caira, M. R.; Nassimbeni, L. R.; Russell, J. C. Acta Crystallogr. B. 1977, B33, 1171-1176.
16. See, for instance, (a) Palenik, G. J.; Bentley, J. A. J. Am. Chem. Soc. 1978, 100, 2863-2867. (b) Caira, M. R.; Nassimbeni, L. R.; Russell, J. C. Acta Crystallogr. B. 1977, B33, 1171-1176.
17. Leypold, C. F.; Reiher, M.; Brehm, G.; Schmitt, M. O.; Schneider, S.; Matousek, P.; Towrie, M. Phys. Chem. Chem. Phys. 2003, 5, 1149-1157.
18. Othersen, O. G.; Beierlein, F.; Lanig, H.; Clark, T. J. Phys. Chem. B 2003, 107, 13743-13749.
19. Gulbis, J.; Everett, G. W., Jr. Tetrahedron 1976, 32, 913-917.
20. (a) Becke, A. D. J. Chem. Phys. 1993, 98, 1372-1377.
21. (b) Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
22. (c) Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.; Frisch, M. J. J. Phys. Chem. 1994, 98, 11623-11627.
23. (a) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789.
24. (b) Miehlich, B.; Savin, A.; Stoll, H.; Preuss, H. Chem. Phys. Lett. 1989, 157, 200-206.
25. (a) Ditchfield, R.; Hehre, W. J.; Pople, J. A. J. Chem. Phys. 1971, 54, 724-728.
26. (b) Hehre, W. J.; Ditchfield, R.; Pople, J. A. J. Chem. Phys. 1972, 56, 2257-2261.
27. (c) Hariharan, P. C.; Pople, J. A. Mol. Phys. 1974, 27, 209-214.
28. (d) Gordon, M. S. Chem. Phys. Lett. 1980, 76, 163-168.
29. (e) Hariharan, P. C.; Pople, J. A. Theor. Chim. Acta 1973, 28, 213-222.
30. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; 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. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A. 11.3; Gaussian, Inc.: Pittsburgh, PA, 2002.
31. Barone, V.; Cossi, M.; Tomasi, J. J. Chem. Phys. 1997, 107, 3210-3221.
32. (a) Frisch, M. J.; Head-Gordon, M.; Pople, J. A. Chem. Phys. Lett. 1990, 166, 275-280.
33. (b) Frisch, M. J.; Head-Gordon, M.; Pople, J. A. Chem. Phys. Lett. 1990, 166, 281-289.
34. (c) Pople, J. A.; Krishnan, R.; Schlegel, H. B.; Binkley, J. S. Int. J. Quantum Chem., Quantum Chem. Symp. 1979, 13, 225-241.
35. (d) Handy, N. C.; Schaefer, H. F., III. J. Chem. Phys. 1984, 81, 5031-5033.
36. (a) Wolinski, K.; Hinton, J. F.; Pulay, P. J. Am. Chem. Soc. 1990, 112, 8251-8260.
37. (b) Dodds, J. L.; McWeeny, R.; Sadlej, A. J. Mol. Phys. 1980, 41, 1419.
38. (c) Ditchfield, R. Mol. Phys., 1974, 27, 789-807.
39. van Eikema Hommes, N. J. R.; Clark, T. J. Mol. Model. 2004, 10, in press.
40. Clark, T.; Chandrasekhar, J. Isr. J. Chem. 1994, 33, 435-448.
41. Clark, T.; Alex, A.; Beck, B.; Burkhardt, F.; Chandrasekhar, J.; Gedeck, P.; Horn, A. H. C.; Hutter, M.; Martin, B.; Rauhut, G.; Sauer, W.; Schindler, T.; Steinke, T. Vamp 8.1, Erlangen, 2002.
42. (a) Dewar, M. J. S.; Zoebisch, E. G.; Healy, E. F.; Stewart, J. J. P. J. Am. Chem. Soc. 1985, 107, 3902-3909.
43. (b) Holder, A. J. In Encyclopedia of Computational Chemistry; Schleyer, P. v. R., Allinger, N. L., Clark, T., Gasteiger, J., Kollman, P. A., Schaefer, H. F., III, Schreiner, P. R., Eds.; John Wiley & Sons Ltd.: Chichester, U.K., 1998; pp 8-11.
44. Rauhut, G.; Clark, T.; Steinke, T. J. Am. Chem. Soc. 1993, 115, 9174-9181.
45. Gedeck, P.; Schneider, S. J. Photochem. Photobiol., A 1997, 105, 165-182.
46. Schneider, S.; Schmitt, M. O.; Brehm, G.; Reiher, M.; Matousek, P.; Towrie, M. Photochem. Photobiol. Sci. 2003, 2, 1107-1117.
47. Schneider, S.; Clark, T. Manuscript in preparation, to be submitted to J. Phys. Chem.
48. Schneider, S.; Schmitt, M. O.; Brehm, G.; Fritz, N. Central Laser Facility Annual Report 2002/2003, 116-118.
49. Hughes, L. J.; Stezowski, J. J.; Hughes, R. E. J. Am. Chem. Soc. 1979, 101, 7655-7656.