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G4391

Sigma-Aldrich

Gly-Arg-Gly-Asp-Ser

≥97% (HPLC)

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About This Item

Empirical Formula (Hill Notation):
C17H30N8O9
CAS Number:
Molecular Weight:
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 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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Hong Y Cho et al.
Biomacromolecules, 11(9), 2199-2203 (2010-09-14)
Poly(ethylene glycol) (PEG) star polymers containing GRGDS (Gly-Arg-Gly-Asp-Ser) peptide sequences on the star periphery were synthesized by atom transfer radical polymerization (ATRP) of poly(ethylene glycol) methyl ether methacrylate (PEGMA), GRGDS modified poly(ethylene glycol) acrylate (GRGDS-PEG-Acryl), fluorescein o-methacrylate (FMA), and ethylene
Yukie Aizawa et al.
Biomaterials, 33(21), 5198-5205 (2012-05-09)
Cell-cell interactions are critical to understanding functional tissues. A number of stem cell populations have been shown to receive key regulatory information from endothelial cells (ECs); however, the role of ECs in the retinal stem and progenitor cell (RSPC) niche
Yves Lecarpentier et al.
Cells, 9(6) (2020-06-25)
Mesenchymal stromal cells (MSCs) were obtained from human bone marrow and amplified in cultures supplemented with human platelet lysate. Once semi-confluent, cells were seeded in solid collagen scaffolds that were rapidly colonized by the cells generating a 3D cell scaffold.
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
A Faik et al.
European journal of biochemistry, 253(3), 552-559 (1998-07-08)
Using a polyclonal antibody (P23) generated against the human platelet integrin aIIb beta3 and a FITC-conjugate secondary antibody, fluorescence is observed at the surface of protoplasts isolated from Arabidopsis thaliana and Rubus fruticosus. Arabidopsis thaliana cells grown in suspension culture

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