Unusual peptides containing the 2,6-diaminopimelic acid framework: Stereocontrolled synthesis, X-ray analysis, and computational modelling. Part 2

Tetrahedron Asymmetry

Volumn 14, Issue 17, 2003, Pages 2639-2649

  Galeazzi, R ^a   Garavelli, M ^b   Grandi, A ^b   Monari, M ^b   Porzi, G ^b   Sandri, S ^b  

^a UNIVERSITÀ POLITECNICA DELLE MARCHE   (Italy)

^b UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

1 (2' KETO 3' ISOPROPYL 1',4' DIAZABICYCLO[4.3.0] 4' NONEN 6' YL) 3 (2'' ETHOXY 3'',6'' DIHYDRO 3'' ISOPROPYL 5'' PIRAZINON 6'' YL)PROPANE; 8 (2',5' DIKETO 3' ISOPROPYL 1',4' DIAZABICYCLO[4.3.0]NON 6' YL) 3 AZA 5 AMINO 4 KETO 2 ISOPROPYL 5 METHYLETHYLOCTANOATE; 8 (2',5' DIKETO 3' ISOPROPYL 1',4' DIAZABICYCLO[4.3.0]NON 6' YL) 3 AZA 5 AMINO 4 KETO 2 ISOPROPYLETHYLOCTANOATE; 8 (2',5' DIKETO 3' ISOPROPYL 1',4' DIAZABICYCLO[4.3.0]NON 6' YL) 3 AZA 5 AMINO 5 BENZYL 4 KETO 2 ISOPROPYLETHYLOCTANOATE; DIAMINOPIMELIC ACID; PEPTIDE; PROTEIN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CALCULATION; CRYSTAL STRUCTURE; DRUG CONFORMATION; DRUG STRUCTURE; DRUG SYNTHESIS; MODEL; PRIORITY JOURNAL; PROTEIN ANALYSIS; PROTEIN VARIANT; PROTON NUCLEAR MAGNETIC RESONANCE; X RAY ANALYSIS;

EID: 0041829504     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(03)00541-X     Document Type: Article

References (48)

1. Paradisi F., Porzi G., Sandri S. Tetrahedron: Asymmetry. 12:2001;3319-3324.
2. Gelb M.H., Lin Y., Pickard M.A., Song Y., Vederas J.C. J. Am. Chem. Soc. 112:1990;4932-4942.
3. Williams R.M., Fegley G.J., Gallegos R., Schaefer F., Pruess D.L. Tetrahedron. 52:1996;1149-1164.
4. Bull S.D., Chernega A.N., Davies S.G., Moss W.O., Parkin R.M. Tetrahedron. 54:1998;10379-10388.
5. Williams R.M., Myeong-Nyeo Im, Cao J. J. Am. Chem. Soc. 113:1991;6976-6981.
6. Satyanarayana S., Grossert J.S., Lee S.F., White R.L. Can. Amino Acids. 21:2001;221-235.
7. Kubasch N., Schmidt R.R. Eur. J. Org. Chem. 2002;2710-2726.
8. Bouchaudon J., Dutruc-Rosset G., Farge D., James C. J. Chem. Soc., Perkin Trans. 1. 1989;695-701.
9. Bull S.D., Davies S.G., Parkin R.M., Sanchez-Sancho F. J. Chem. Soc., Perkin Trans. 1. 1998;2313-2320.
10. Favero V., Porzi G., Sandri S. Tetrahedron: Asymmetry. 8:1997;599-612.
11. Di Felice P., Porzi G., Sandri S. Tetrahedron: Asymmetry. 10:1999;2191-2201.
12. Porzi G., Sandri S., Verrocchio P. Tetrahedron: Asymmetry. 9:1998;119-132.
13. Ab initio calculations were carried out by using a Gaussian-98 W2.1 program and full geometry optimizations were performed at the RB3LYP/6-311G(d) level.
14. Trabocchi A., Occhiato E.G., Potenza D., Guarna A. J. Org. Chem. 67:2002;7483-7492.
15. Fernandez M.M., Diez A., Rubiralta M., Montenegro E., Casamitjana N. J. Org. Chem. 67:2002;7587-7599.
16. Belvisi L., Bernardi A., Manzoni L., Potenza D., Scolastico C. Eur. J. Org. Chem. 2000;2563-2569.
17. Belvisi L., Gennai C., Mielgo A., Potenza D., Scolastico C. Eur. J. Org. Chem. 1999;389-400.
18. Mazza F., Lucente G., Pinnen F., Zanotti G. Acta Crystallogr. C40:1984;1974-1976.
19. Weiner S.J., Kollman P.A., Nguyen D.T., Case D.A. J. Comput. Chem. 4:1986;230-252.
20. Chang G., Guida W.C., Still W.C. J. Am. Chem. Soc. 111:1989;4379-4386.
21. Wolinski K., Hilton J.F., Pulay P. J. Am. Chem. Soc. 112:1990;8251-8260.
22. Wolinski K., Sadlej A. Mol. Phys. 41:1980;1419-1430.
23. Ditchfield R. Mol. Phys. 27:1974;789-807.
24. McWeeny R. Phys. Rev. 126:1962;1024-1028.
25. London F. J. Phys. Radium. 8:1937;397-409.
26. Bagno A. Chem. Eur. J. 7:2001;1652-1660.
27. 2-CHO) placed at crystallographic positions and simulating the intermolecular hydrogen bonding network around a monomer as seen in the X-ray resolved trimer (see Fig. 3).
28. Sanz-Cervera J.F., Williams R.M., Alberto Marco J., Lopez-Sanchez J.M., Gonzalez F., Martinez M.E., Sancenon F. Tetrahedron. 56:2000;6345-6358.
29. Piccinelli F., Porzi G., Sandri M., Sandri S. Tetrahedron: Asymmetry. 14:2003;393-398.
30. Paradisi F., Piccinelli F., Porzi G., Sandri S. Tetrahedron: Asymmetry. 13:2002;497-502.
31. Ferioli F., Piccinelli F., Porzi G., Sandri S. Tetrahedron: Asymmetry. 13:2002;1181-1187.
32. Paradisi F., Porzi G., Rinaldi S., Sandri S. Tetrahedron: Asymmetry. 11:2000;4617-4622.
33. Paradisi F., Porzi G., Rinaldi S., Sandri S. Tetrahedron: Asymmetry. 11:2000;1259-1262.
34. SMART & SAINT Software Reference Manuals, version 5.051 (Windows NT Version), Bruker Analytical X-ray Instruments Inc.: Madison, WI, 1998.
35. Sheldrick, G. M. SADABS: Program for Empirical Absorption Correction; University of Göttingen, Germany, 1996.
36. Altomare A., Burla M.C., Cavalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G., Spagna R. J. Appl. Crystallogr. 32:1999;115-119.
37. Sheldrick, G. M. SHELXTLplus Version 5.1 (Windows NT version) Structure Determination Package; Bruker Analytical X-ray Instruments Inc.: Madison, WI, 1998.
38. Mohamadi F., Richards N.G.J., Guida W.C., Liskamp R., Lipton M., Caulfield C., Chang G., Hendrickson T., Still W.C. J. Comput. Chem. 11:1990;440-467.
39. McDonald D.Q., Still W.C. J. Org. Chem. 61:1996;1385-1391.
40. Still W.C., Tempczyk A., Hawley R.C., Hendrickson T. J. Am. Chem. Soc. 12:1990;6127-6129.
41. 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.; Millan, 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.; Patersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malik, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; 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.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzales, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. Gaussian 98, Revision A.9, Gaussian Inc., Pittsburgh, PA, 1998.
42. Becke A.D. J. Chem. Phys. 98:1993;5648-5652.
43. Gonzalez L., Mo O., Yanez M. J. Comput. Chem. 18:1997;1124-1135.
44. Klein R.A. J. Comput. Chem. 23:2002;585-599.
45. Novoa J.J., Sosa C. J. Phys. Chem. 99:1995;15837-15845.
46. Brunel L., Carre' F., Dutremez S.G., Guerin C., Dahan F., Eisenstein O., Sini G. Organometallics. 20:2001;47-54.
47. Bernardi F., Garavelli M., Scatizzi M., Tomasini C., Trigari V., Crisma M., Formaggio F., Peggion C., Toniolo C. Chem. Eur. J. 8:2002;2516-2525.
48. Tomasini C., Trigari V., Lucarini S., Bernardi F., Garavelli M., Peggion C., Formaggio F., Toniolo C. Eur. J. Org. Chem. 2003;259-267.