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G5779

Sigma-Aldrich

Gly-Pro-Arg-Pro amide

≥97% (HPLC)

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C18H32N8O4
CAS Number:
126047-75-4
Molecular Weight:
424.50
MDL number:
MFCD00237962
UNSPSC Code:
12352209
PubChem Substance ID:
24895231
NACRES:
NA.32

Assay

≥97% (HPLC)

UniProt accession no.

P02751
P04937
P11276

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
Leonardo Pasalic et al.
Methods in molecular biology (Clifton, N.J.), 1646, 369-389 (2017-08-15)
Flow cytometry is a powerful tool for rapid evaluation of multiple functional properties of large numbers of platelets in whole blood. In the following chapter, we provide a number of flow cytometry-based protocols broadly aimed at (1) assessment of constitutively
K Kawasaki et al.
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
Christine S M Lee et al.
Methods in molecular biology (Clifton, N.J.), 2663, 441-461 (2023-05-19)
Heparin-induced thrombocytopenia (HIT) is a well-characterized, iatrogenic complication of heparin anticoagulation with significant morbidity. In contrast, vaccine-induced immune thrombotic thrombocytopenia (VITT) is a recently recognized severe prothrombotic complication of adenoviral vaccines, including the ChAdOx1 nCoV-19 (Vaxzevria, AstraZeneca) and Ad26.COV2.S (Janssen
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