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Merck

G4391

Sigma-Aldrich

Gly-Arg-Gly-Asp-Ser

≥97% (HPLC)

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About This Item

Fórmula empírica (notación de Hill):
C17H30N8O9
Número de CAS:
Peso molecular:
490.47
MDL number:
UNSPSC Code:
12352209
PubChem Substance ID:
NACRES:
NA.32

Quality Level

assay

≥97% (HPLC)

form

powder

composition

Peptide content, ≥60%

technique(s)

blocking: suitable
cell culture | mammalian: suitable

storage temp.

−20°C

SMILES string

NCC(=O)N[C@@H](CCCNC(N)=N)C(=O)NCC(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CO)C(O)=O

InChI

1S/C17H30N8O9/c18-5-11(27)23-8(2-1-3-21-17(19)20)14(31)22-6-12(28)24-9(4-13(29)30)15(32)25-10(7-26)16(33)34/h8-10,26H,1-7,18H2,(H,22,31)(H,23,27)(H,24,28)(H,25,32)(H,29,30)(H,33,34)(H4,19,20,21)/t8-,9-,10-/m0/s1

InChI key

RGNVSYKVCGAEHK-GUBZILKMSA-N

Gene Information

human ... ITGB3(3690)

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Amino Acid Sequence

Gly-Arg-Gly-Asp-Ser

General description

Gly-Arg-Gly-Asp-Ser peptide sequence is identical to the cell-binding region of fibronectin protein. Arg-Gly-Asp (RGD) region is found in various proteins, and is crucial for facilitating cell-adhesive activity.

Application

Gly-Arg-Gly-Asp-Ser has been used-
  • as an antigen to determine whether integrin α4 or α5 hinders the adhesion of day 3 postirradiation thymocytes to thymic epithelial cells, in mice
  • for the treatment of collagen IV-coated dishes to study the role of integrins α1, αv, β1, and β3 in Sca-1+ progenitor cell differentiation into SMCs (smooth muscle cells)
  • as a blocking peptide for the pre-incubation of Nisseria meningitides strains, to perform blocking experiments to study the interactions between these bacterial strains and fibronectin
  • for the pre-treatment of EL-4 cells infected by AdCMV-GFP (cytomegalovirus-green fluorescent protein), to study whether interaction with cellular integrins is essential for the transduction of adenovirus

Biochem/physiol Actions

Antagonist of integrin function
Gly-Arg-Gly-Asp-Ser inhibits metastasis in syngeneic mice or in mice lacking platelet function, when co-injected with B16-Fl0 melanoma cells.

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)


Certificados de análisis (COA)

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Biomacromolecules, 8(12), 3977-3983 (2007-11-28)
T Eberhard et al.
Infection and immunity, 66(4), 1791-1794 (1998-04-07)
Adhesion of Neisseria meningitidis strains to extracellular matrix (ECM) and purified matrix components was examined. Most strains bound to subendothelial ECM as well as to immobilized fibronectin and types I, III, and V collagen. Strains from healthy carriers adhered significantly
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R P Leon et al.
Proceedings of the National Academy of Sciences of the United States of America, 95(22), 13159-13164 (1998-10-28)
Although adenovirus can infect a wide range of cell types, lymphocytes are not generally susceptible to adenovirus infection, in part because of the absence of the expression of the cellular receptor for the adenoviral fiber protein. The cellular receptor for

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