1H-NMR determination of the solution structure and absolute configuration of FR134043, a novel inhibitor of human leukocyte elastase

Journal of Peptide Research

Volumn 55, Issue 2, 2000, Pages 120-128

  Nakanishi, Isao ^a   Fujikawa, A ^a   Imai, K ^a   Sato, A ^a  

^a ASTELLAS PHARMA INC   (Japan)

Author keywords

2D NMR; Absolute configuration; Elastase inhibitor; FR134043; Macrocyclic compound; Simulated annealing; Solution structure

Indexed keywords

FR 134043; FR 901277; LEUKOCYTE ELASTASE INHIBITOR; NATURAL PRODUCT; UNCLASSIFIED DRUG; HETEROCYCLIC COMPOUND; HYDROGEN; LEUKOCYTE ELASTASE; SERINE PROTEINASE INHIBITOR;

ARTICLE; CHIRALITY; CONTROLLED STUDY; DRUG STRUCTURE; NUCLEAR OVERHAUSER EFFECT; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOISOMERISM; STRUCTURE ANALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; DRUG ANTAGONISM; HUMAN; NUCLEAR MAGNETIC RESONANCE; SOLUTION AND SOLUBILITY;

HETEROCYCLIC COMPOUNDS; HUMANS; HYDROGEN; LEUKOCYTE ELASTASE; MODELS, MOLECULAR; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; SERINE PROTEINASE INHIBITORS; SOLUTIONS;

EID: 0033624989     PISSN: 1397002X     EISSN: None     Source Type: Journal    
DOI: 10.1034/j.1399-3011.2000.00165.x     Document Type: Article

References (34)

1. 1. Tanaka, H., Kuroda, A., Marusawa, H. et al. (1987) Structure of FK506: a novel immunosuppressant isolated from Streptomyces. J. Am. Chem. Soc. 109, 5031-5033.
2. 2. Sehgal, S.N., Baker, H. & Vezina, C. (1975) Rapamycin (AY-22,989), a new antifungal antibiotic II. Fermentation, isolation and characterization. J. Antibiot. 28, 727-732.
3. 3. Rüegger, A., Kuhn, M., Lichti, H. et al. (1976) Cyclosporin A, ein immunsuppressiv wirksamer peptidmetabolit aus Trichoderma polysporum (Link ex Pers.) Rifai. Helv. Chim. Acta 59, 1075-1092.
4. 4. Gause, G.F. & Brazhnikova, M.G. (1944) Gramicidin S and its use in the treatment of infected wounds. Nature 154, 703-703.
5. 5. Brockmann, H. & Schmidt-Kastner, G. (1955) Valinomycin I, XXVII. Mitteil. über antibiotica aus Actinomyceten. Chem. Ber. 88, 57-61.
6. 6. Pagano, J.F., Weinstein, M.J., Stout, H.A. & Donovick, R. (1956) Thiostrepton, a new antibiotic - (I) in vitro studies. Antibiot. Ann. 1956, 554-559.
7. 7. Fujie, K., Shinguh, Y., Hatanaka, H. et al. (1993) FR901277, a novel inhibitor of human leukocyte elastase from Streptomyces resistomycificus. Producing organism, fermentation, isolation, physicochemical and biological properties. J. Antibiot. 46, 908-913.
8. 8. Falk, M., Spierenburg, P.F. & Walter, J.A. (1996) Determination of the stereochemistry of natural products from nuclear magnetic resonance data by constrained molecular dynamics. J. Comput. Chem. 17, 409-417.
9. 9. Reggelin, M., Hoffmann, H., Kock, M. & Mierke, D.F. (1992) Determination of conformation and relative configuration of a small, rapidly tumbling molecule in solution by combined application of NOESY and restrained MD calculations. J. Am. Chem. Soc. 114, 3272-3277.
10. 10. Kline, T., Mueller, L., McMaser, E.S., Lau, W.F. & Mayers, C.A. (1996) A pseudopeptide incorporating the tetrahydrophthalazinc nucleus, a constrained Aza analog of phenylalanine. Int. J. Peptide Protein Res. 47, 142-147.
11. 11. Karuso, P., Kessler, H. & Mierke, D.F. (1990) Solution structure of FK506 from nuclear magnetic resonance and molecular dynamics. J. Am. Chem. Soc. 112, 9434-9436.
12. 12. Michnick, S.W., Rosen, M.K., Wandless, T.J., Karplus, M. & Schreiber, S.L. (1991) Solution structure of FKBP, a rotamase enzyme and receptor for FK506 and rapamycin. Science 252, 836-839.
13. 13. Powers, R., Garett, D.S., March, C.J., Frieden, E.A., Gronenborn, A.M. & Clore, G.M. (1993) The high-resolution, three-dimensional solution structure of human interleukin-4 determined by multidimensional heteronuclear magnetic resonance spectroscopy. Biochemistry 32, 6744-6762.
14. 1H-NMR and distance geometry. Int. J. Peptide Protein Res. 41, 433-440.
15. 15. Fujikawa, A., Nakanishi, I., Sato, A., Fujioka, M. & Yasuda, T. (1995) Conformational study of FR134043, a novel inhibitor of human leukocyte elastase. Peptide Chem 1995, 437-440.
16. 1H NMR spectra of proteins via double quantum filtering. Biochem. Biophys. Res. Commun. 117, 479-485.
17. 1H NMR spectra via two-dimensional homonuclear Hartmann-Hahn spectroscopy. J. Am. Chem. Soc. 107, 2820-2821.
18. 18. Kumar, A., Ernst, R.R. & Wüthrich, K. (1980) A two-dimensional nuclear Overhauser enhancement (2D NOE) experiment for the elucidation of complete proton-proton cross-relation networks in biological macromolecules. Biochem. Biophys. Res. Commun. 95, 1-6.
19. 19. Bodenhausen, G., Kogler, H. & Ernst, R.R. (1984) Selection of coherence-transfer pathways in NMR pulse experiments. J. Magn. Reson. 58, 370-388.
20. 20. Dauber-Osguthorpe, P., Roberts, V.A., Osguthorpe, D.J., Wölff, J., Genest, M. & Hagler, A.T. (1988) Structure and energetics of ligand binding to proteins: Escherichia coli dihydrofolate reductase-trimethoprim, a drug-receptor system. Proteins Struct. Func. Genet. 4, 31-47.
21. 21. Wüthrich, K., Wider, G., Wagner, G. & Braun, W. (1982) Sequential resonance assignments as a basis for determination of spatial protein structures by high resolution proton nuclear magnetic resonance. J. Mol. Biol. 155, 311-319.
22. 1H nuclear magnetic resonance spectra. Computation of sterically allowed proton-proton distances and statistical analysis of proton-proton distances in single crystal protein conformations. J. Mol. Biol. 155, 321-346.
23. 1H-NMR spectra of polypeptides and proteins. Biopolymers 22, 131-138.
24. 1H-NMR assignment and secondary structure of human insulin-like growth factor-I (IGF-I) in solution. J. Biochem. 111, 529-536.
25. 25. Steiner, J.R. & Barnes, C.L. (1988) Crystal and molecular structure of Destruxin B. Int. J. Peptide Protein Res. 31, 212-219.
26. 26. Ginell, S., Lessinger, L. & Berman, H.M. (1988) The crystal and molecular structure of the anticancer drug actinomycin D. Some explanations for its unusual properties. Biopolymers 27, 843-864.
27. 27. Loosli, H.R., Kessler, H., Oschkinat, H., Weber, H.P., Petcher, T.J. & Widmer, A. (1985) The conformation of cyclosporin A in the crystal and in solution. Helv. Chim. Acta 68, 682-704.
28. 28. Rose, G.D., Gierasch, L.M. & Smith, J.A. (1985) Turns in peptides and proteins. Adv. Protein Chem. 37, 1-109.
29. 29. Weibhoff, H., Wieprecht, T., Henklein, P., Frömmel, C., Antz, C. & Mügge, C. (1996) Comparison of proline and N-methylnorleucine induced conformational equilibria in cyclic pentapeptides. FEBS Lett 387, 201-207.
30. H-isopropyl-L-alaninamide. Int. J. Peptide Protein Res. 17, 469-479.
31. 31. Schrauber, H., Eisenhaber, F. & Argos, P. (1993) Rotamers: to be or not to be? An analysis of amino acid side-chain conformations in globular proteins. J. Mol. Biol. 230, 592-612.
32. 32. Zimmerman, S.S., Pottle, M.S.N., Némethy, G. & Scheraga, H.A. (1977) Conformational analysis of the 20 naturally occurring amino acid residues using ECEPP. Macromolecules 10, 1-9.
33. 33. Bode, W., Meyer, E. Jr & Powers, J.C. (1989) Human leukocyte and procine pancreatic elastase: X-ray crystal structures, mechanism, substrate specificity, and mechanism-based inhibitors. Biochemistry 28, 1951-1963.
34. 34. Nakanishi, I., Kinoshita, T., Tada, T., Fujita, T., Hatanaka, H. & Sato, A. (1999) Molecular structure of FR901277, a novel inhibitor of human leukocyte elastase, and its binding mode simulation. Bioorg. Med. Chem. Lett. 9, 2397-2402.