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Merck

G5779

Sigma-Aldrich

Gly-Pro-Arg-Pro amide

≥97% (HPLC)

Sinónimos:

GPRP amide, Glycine-Proline-Arginine-Proline amide, Glycyl-L-prolyl-L-arginyl-L-prolinamide

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About This Item

Fórmula empírica (notación de Hill):
C18H32N8O4
Número de CAS:
Peso molecular:
424.50
MDL number:
UNSPSC Code:
12352209
PubChem Substance ID:
NACRES:
NA.32

Quality Level

assay

≥97% (HPLC)

UniProt accession no.

storage temp.

−20°C

SMILES string

NCC(=O)N1CCC[C@H]1C(=O)N[C@@H](CCCNC(N)=N)C(=O)N2CCC[C@H]2C(N)=O

InChI

1S/C18H32N8O4/c19-10-14(27)25-8-3-6-13(25)16(29)24-11(4-1-7-23-18(21)22)17(30)26-9-2-5-12(26)15(20)28/h11-13H,1-10,19H2,(H2,20,28)(H,24,29)(H4,21,22,23)/t11-,12-,13-/m0/s1

InChI key

SCCTZYGEMPQRCV-AVGNSLFASA-N

Gene Information

human ... FN1(2335)
mouse ... FN1(14268)
rat ... FN1(25661)

Amino Acid Sequence

Gly-Pro-Arg-Pro-NH2

General description

Gly-Pro-Arg-Pro is a peptide that mimics the N-terminal Gly-Pro-Arg region in the a chain of fibrin protein.

Application

Gly-Pro-Arg-Pro amide has been used-
  • as a constituent of buffer during fluid-phase and bound thrombin inhibition assays, to determine the activity of thrombin
  • for blocking fibrin polymerization and preventing fibrin clot formation in presence of α-thrombin, in blood obtained from mice
  • during preparation of human soluble fibrin, to block the polymerization of soluble fibrin

Biochem/physiol Actions

Gly-Pro-Arg-Pro peptide suppresses the early steps of fibrin polymerization. The amide derivative of this peptide prevents the degradation of fibrinogen and fragment D by plasmin, even in the presence of EGTA (ethylene glycol-bis(β-aminoethyl ether)-N,N,N′,N′-tetraacetic acid).

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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Chemical & pharmaceutical bulletin, 40(12), 3253-3260 (1992-12-01)
N-Terminal tetrapeptide analogs of fibrin alpha-chain were synthesized by the solution method using a new active ester, the ester of the oxime of p-nitroacetophenone, and by the solid-phase method. Their inhibitory effects on fibrinogen/thrombin clotting were examined. Of the synthetic
P C Liaw et al.
The Journal of biological chemistry, 276(24), 20959-20965 (2001-04-11)
Although fibrin-bound thrombin is resistant to inactivation by heparin.antithrombin and heparin.heparin cofactor II complexes, indirect studies in plasma systems suggest that the dermatan sulfate.heparin cofactor II complex can inhibit fibrin-bound thrombin. Herein we demonstrate that fibrin monomer produces a 240-fold
P Klement et al.
Journal of thrombosis and haemostasis : JTH, 1(3), 587-594 (2003-07-23)
Although hirudin is better than heparin at preventing recurrent ischemia in patients with unstable angina, hirudin produces more bleeding. The purpose of this study was to use a rabbit arterial thrombosis prevention and ear bleeding model to determine whether for

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