Linear analogues derived from the first EGF-like domain of human blood coagulation factor VII: Enhanced inhibition of FVIIa/TF complex activity by backbone modification through aspartimide formation

Journal of Peptide Science

Volumn 5, Issue 7, 1999, Pages 323-329

  Husbyn, Mette ^a,b   Ørning, Lars ^a   Cuthbertson, Alan ^a   Fischer, Peter M ^a  

^a NYCOMED IMAGING AS   (Norway)

^b UNIVERSITY OF OSLO   (Norway)

Author keywords

Aspartimide formation; EGF1 like domain; FX activation; Human FVII; Peptide synthesis

Indexed keywords

ASPARTIMIDE; BLOOD CLOTTING FACTOR 7; BLOOD CLOTTING FACTOR 7A; CYSTEINE; EPIDERMAL GROWTH FACTOR; IMIDE; THROMBOPLASTIN; UNCLASSIFIED DRUG;

AMINO ACID SEQUENCE; ANALYTIC METHOD; ARTICLE; BLOOD CLOTTING; COMPLEX FORMATION; ENZYME ACTIVITY; PEPTIDE SYNTHESIS; PRIORITY JOURNAL; PROTEIN ANALYSIS; PROTEIN MODIFICATION; PROTEIN PURIFICATION;

AMINO ACID SEQUENCE; ASPARTIC ACID; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; EPIDERMAL GROWTH FACTOR; FACTOR VII; HUMANS; MOLECULAR SEQUENCE DATA; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0032783370     PISSN: 10752617     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-1387(199907)5:7<323::AID-PSC201>3.0.CO;2-B     Document Type: Article

References (25)

1. Rapaport SI, Rao LVM. The tissue factor pathway: How it has become a prima ballerina. Thromb Haemost 1995; 74: 7-17.
2. Hagen FS, Gray CL, O'Hara PJ, Grant FJ, Saari GC, Woodbury RG, Hart CE, Insley M, Kisiel W, Kurachi K, Davie EW. Characterization of a cDNA coding for human factor VII. Proc Natl Acad Sci 1986; 83: 2412-2416.
3. O'Hara PJ, Grant FJ, Haldeman BA, Gray CL, Insley MY, Hagen FS, Murray MJ. Nucleotide sequence of the gene coding for human factor VII, a vitamin K-dependent protein participating In blood coagulation. Proc Natl Acad Sci 1987; 84: 5158-5162.
4. Nemerson Y. Thrombosis and hemostasis. Blood 1988; 71: 1-8.
5. Davie EW. Biochemical and molecular aspects of the coagulation cascade. Thromb Haemost 1995; 74: 1-6.
6. Furie B, Furie BC. The molecular basis of blood coagulation. Cell 1988; 53: 505-518.
7. Kirchhofer D, Banner DW. Molecular and structural advances in tissue factor-dependent coagulation. Trends Cardiovasc Med 1997; 7: 316-324.
8. Banner DW, D'Arcy A, Chene C, Winkler FK, Guha A, Konigsberg WH, Nemerson Y, Kirchhofer D. The crystal structure of the complex of blood coagulation, factor vIIa with soluble tissue factor. Nature 1996; 380: 41-46.
9. Kavlie A, Orning L, Grindflek A, Stormorken H, Prydz H. Characterization of a factor VII molecule carrying a mutation in the second epidermal growth factor. Thromb Haemost 1998; 79: 1136-1143.
10. Barstad RM, Stormorken H, Orning L, Stephens RW, Petersen LB, Kierulf P, Sakariassen KS. Reduced thrombus formation In native blood of homozygous factor VII-deficient patients at high arterial wall shear rate. Blood 1994; 84: 3371-3377.
11. Husbyn M, Ørning L, Sakariassen KS, Fischer PM. Peptides corresponding to the second epidermal growth factor-like domain of human blood coagulation factor VII: Synthesis, folding and biological activity. J Peptide Res 1997; 50: 475-482.
12. Barany G, Merrifield RB, Gross EIn, Meienhofer J. The Peptides, Solid Phase Peptide Synthesis, pp. 1-284, Academic Press, New York, 1979.
13. Bodanszky M, Martinez, J, Gross EIn, Meienhofer J. The Peptides, Side Reactions in Peptide Synthesis, pp. 111-216, Academic Press, New York, 1983.
14. Capasso S, Mazzarella L, Zagari A. Deamidation via cyclic imide of asparaginyl peptides: Dependence on salts, buffers and organic solvents. Peptide Res 1991; 4: 234-238.
15. King DS, Fields CG, Fields GB. A cleavage method which minimizes side reactions following Fmoc solid phase synthesis. Int J Peptide Prot Res 1990; 36: 255-266.
16. Stephenson RC, Clarke S. Succinimide formation from aspartyl and asparaginyl peptides as a model for the spontaneous degradation of proteins. J Biol Chem 1984; 264: 6164-6170.
17. Yang Y, Sweeney WV, Schneider K, Thornqvist S, Chait BT, Tam JP. Aspartimide formation in base driven fluorenylmethoxycarbonyl chemistry. Tetrahedron Lett 1994; 35: 9689-9692.
18. Teshima G, Stults JT, Ling V, Canova-Davis E. Isolation and characterization of a succinimide variant of methionyl human growth hormone. J Biol Chem 1991; 266: 13544-13547.
19. Hayakawa YJ. Inclusion of a beta-aspartyl peptide bond causes a loss of inherent biological activities. Biochemistry 1994; 115: 15.
20. Bischoff R, Kolbe HVJ. Deamidation of asparagine and glutamine residues in proteins and peptides. Structural determinants and analytical methodology. J Chrom 1994; 662: 261-278.
21. Wright H. Sequence and structure determinants of the nonenzymatic deamidation of glutamine and asparagine residues in proteins. Prot Eng 1991; 4: 283-294.
22. Murray ED, Clarke S. Synthetic peptide substrates for erythrocyte protein carboxyl methyltransferase. Detection of a new site of methylation at isomerized L-aspartyl residues. J Biol Chem 1984; 259: 10722-10732.
23. Leonard BJN, Chen Q, Blajchman MA, Ofosu FA, Sridhara S, Yang D, Clarke BJ. Factor VII deficiency caused by a structural variant N57D of the first epidermal growth factor domain. Blood 1998; 91: 142-148.
24. Muranyi A, Finn BE, Gippert GP, Forsen S, Stenflo J, Drakenberg T. Solution structure of the N-terminal EGF-like domain from human factor VII. Biochemistry 1998; 37: 10605-10615.
25. 2+ binding to the first epidermal growth factor module of coagulation factor Vila Is Important for cofactor Interaction and proteolytic function. J Biol Chem 1997; 272: 17467-17472.