Conformational study in water by NMR and molecular modeling of cyclic glutamic acid analogues as probes of vitamin K dependent carboxylase

Journal of Chemical Information and Computer Sciences

Volumn 36, Issue 4, 1996, Pages 717-725

  Larue, Valéry ^a   Gharbi Benarous, Josyane ^a   Archer, Francine ^a   Azerad, Robert ^a   Girault, Jean Pierre ^a  

^a UNIVERSITÉ PARIS DESCARTES   (France)

Author keywords

[No Author keywords available]

Indexed keywords

DRUG DERIVATIVE; GLUTAMIC ACID; GLUTAMYL CARBOXYLASE; LIGASE;

ANIMAL; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COMPUTER SIMULATION; CONFORMATION; ENZYMOLOGY; IN VITRO STUDY; LIVER MICROSOME; METABOLISM; MOLECULAR PROBE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; THERMODYNAMICS;

ANIMALS; CARBON-CARBON LIGASES; COMPUTER SIMULATION; GLUTAMIC ACID; LIGASES; MAGNETIC RESONANCE SPECTROSCOPY; MICROSOMES, LIVER; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR PROBES; MOLECULAR STRUCTURE; THERMODYNAMICS;

EID: 0030194703     PISSN: 00952338     EISSN: None     Source Type: Journal    
DOI: 10.1021/ci950153j     Document Type: Article

References (26)

1. Suttie, J. W. Vitamin K-dependent Carboxylase. Ann. Rev. Biochem. 1985, 54, 459-477.
2. Vermeer, C.; De Boer-Van den Berg, M. A. G. Vitamin K-dependent carboxylase. Haematologia 1984, 18, 71-97.
3. Furie, B.; Furie, B. C. The molecular basis of blood coagulation. Cell. 1988, 53, 505-518.
4. Suttie, J. W. In Handbook of Vitamins, 2nd ed.; Machlin, L. J., Ed.; Marcel Dekker, Inc.: New York, 1991; pp 145-194.
5. Finna, J. H.; Goodman, L.; Suttie, J. W. In Vitamin K Metabolism and Vitamin K Dependent Proteins; Suttie, J. W., Ed.; University Park Press: Baltimore. 1980; pp 480-483.
6. Rich, D. H.; Leehrman, S. R.; Kawai, M.; Goodman, H. L.; Suttie, J. W. In Vitamin K Metabolism and Vitamin K dependent Proteins; Suttie, J. W., Ed.; University Park Press: Baltimore, 1980; pp 471-479.
7. Decottignies-Le Marechal, P.; Ducrocq, C.; Marquet, A.; Azerad, R. The stereochemistry of hydrogen abstraction in vitamin K-dependent carboxylation. J. Biol. Chem. 1984, 259, 15010-15012.
8. Azerad, R.; Decottignies-Le Marechal, P.; Ducrocq, C.; Righini-Tapie, A.; Vidal-Cros, A.; Bory, S.; Dubois, J.; Gaudry, M.; Marquet, A. Current Advances in Vitamin K Research; Suttie, J. W., Ed.; Elsevier: New York, 1988; pp 17-24.
9. Soute, B. A. M.; Acher, F.; Azerad, R.; Vermeer, C. Vitamin K-dependent carboxylase: effect of ammonium sulfate on substrate carboxylation and on inhibition by stereospecific substrate analogs. Biochim. Biophys. Acta 1990, 1034, 11-16.
10. Dubois, J.; Gaudry, M.; Bory, S.; Azerad, R.; Marquet, A. Vitamin-K Dependent Carboxylation. Study of the hydrogen abstraction stereochemistry wity γ-fluoroglutamic acid-containing peptides. J. Biol. Chem. 1983, 264, 14145-14150.
11. Ducrocq, C.; Righini-Tapie, A.; Azerad, R.; Green, J. F.; Friedman, P. A.; Beaucourt, J. P.; Rousseau, B. Synthesis of L-glutamic acid stereospecifically labelled at C-4 with tritium: Stereochemistry of tritium release catalyzed by the Vitamin K-dependent carboxylase in the absence of carboxylation. J. Chem. Soc., Perkin Trans. I 1986, 1323-1328.
12. Dubois, J.; Dugave, C.; Foures, C.; Kaminsky, M.; Tabet, J. C.; Bory, S.; Gaudry, M.; Marquet, A. Vitamin-K Dependent Carboxylation - Determination of the Stereochemical Course Using 4-Fluoroglutamyl-Containing Substrate. Biochemistry 1991, 30, 10506-10512.
13. Acher, F.; Azerad, R. Synthesis of Diastereoisomeric Peptides Incorporating Cycloglutamic Acids - Substrate Specificity of Vitamin K-Dependent Carboxylation. Int. J. Peptide Protein Res. 1991, 37, 210-219.
14. Bucourt, R. In Topics in Stereochemistry; Eliel, E. L., Allinger, N. L., Eds.; Wiley: New York, 1974; pp 159-224.
15. Testa, B. In Principles of Organic Stereochemistry; Dekker: New York, 1979; pp 112-113.
16. Cremer, D. A general definition of ring substituent positions, Isr. J. Chem. 1980, 20, 12-19.
17. Fuchs, B. Topics in Stereochemistry; Eliel, E. L., Allinger, N. L.; Wiley: New York, 1978, 10, 1-94.
18. Altona, C.; Sundaralingam, M. Conformational Analysis of the Sugar Ring in Nucleosides and Nucleotides. Improved Metodes for the Interpretation of Proton Magnetic Resonance Coupling Cosntants. J. Am. Chem. Soc. 1973, 95, 2333-2344.
19. Haasnoot, C. A. G.; de Leeuw, F. A. A. M.; Altona, C. The relation between proton-proton NMR coupling constants and substituent electronegativities. I. An empirical generalization of the Karplus equation. Tetrahedron 1980, 36, 2783-2792.
20. Tvaroska, I.; Hricovini, M.; Petrakova, E. An attempt to derive a new Karplus-type equation of vicinal proton-carbon coupling constants for C-O-C-H segments of bonded atoms. Carbohydr. Res. 1989, 189, 359-362.
21. Ladam, P.; Gharbi-Benarous, J.; Pioto, M.; Delaforge, M.; Girault, J. P. Determination of Long-Range 13C-1H Coupling Constants of Macrolide Antibiotics by 2D J-δ Selective INEPT experiments. Magn. Reson. Chem. 1994, 32, 1-7.
22. Morelle, N.; Gharbi-Benarous, J.; Acher, F.; Valle, G.; Crisma, M.; Toniolo, C.; Azerad, R.; Girault, J. P. Conformational Analysis of Cyclohexane-derived Analogues of Glutamic Acid by X-Ray Cristallography, NMR Spectroscopy in Solution, and Molecular Dynamics. J. Chem. Soc., Perkin Trans. 2 1993, 525-.
23. Larue, V.; Gharbi-Benarous, J.; Acher, F.; Valle, G.; Crisma, M.; Toniolo, C.; Azerad, R.; Girault, J. P. Conformational Analysis by NMR Spectroscopy, Molecular Dynamics Simulation in Water and X-Ray Crystallography of Glutamic Acid Analogues: Isomers of 1-Amino-1,3-Cyclopentane Dicarboxylic Acid (ACPD). J. Chem. Soc., Perkin Trans. 2 1995, 1111-1126.
24. Dauber-Osguthorpe, P.; Roberts, V. A.; Osguthorpe, D. J.; Wolff, J.; Genest, M.; Hagler, A. T. Structure and Energetics of Ligand Binding to Proteins: E. coli Dihydrofolate Reductase-Trimethoprim, A Drug-Receptor System. Proteins: Structure, Function Genetics 1988, 4, 31-47.
25. Burt, S. K.; Mackay, D.; Nagler, A. T. In Computer-Aided Drug Design; Perun, T. J., Propst, C. L., Eds.; Marcel Dekker: New York and Basel, 1989; p 66.
26. van Gunsteren, W. F.; Berendsen, H. J. C. Computer Simulation of Molecular Dynamics: Methodology, Applications, and Perspectives in Chemistry. Angew. Chem., Int. Ed. Engl. 1990, 29, 992-1023.