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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:
Molecular Weight:
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 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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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
P Klement et al.
Journal of thrombosis and haemostasis : JTH, 1(3), 587-594 (2003-07-23)
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Methods in molecular biology (Clifton, N.J.), 1967, 305-321 (2019-05-10)
Flow cytometry assessment of platelets using the combination of GSAO [4-(N-(S-glutathionylacetyl)amino)phenylarsonous acid], a dithiol-reactive probe, and P-selectin, a platelet activation marker, is a novel and powerful assay in the identification and quantification of the procoagulant subpopulation of platelets that has

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