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G1269 Sigma-Aldrich

Gly-Arg-Gly-Asp-Ser-Pro-Lys

≥97% (HPLC)

Synonym: GRGDSPK

  • CAS Number 111119-28-9

  • Empirical Formula (Hill Notation) C28H49N11O11

  • Molecular Weight 715.76

  •  MDL number MFCD00076462

  •  PubChem Substance ID 24895055

  •  NACRES NA.32

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Properties

Related Categories Application Index, Biochemicals and Reagents, Cell Biology, Cell Signaling Enzymes, Cell Signaling and Neuroscience,
Quality Level   200
biological source   human
assay   ≥97% (HPLC)
form   powder
application(s)   blocking: suitable
  ligand binding assay: suitable
storage temp.   −20°C
SMILES string   NCCCC[C@H](NC(=O)[C@@H]1CCCN1C(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@H](CCCNC(N)=N)NC(=O)CN)C(O)=O
InChI   1S/C28H49N11O11/c29-8-2-1-5-16(27(49)50)37-25(47)19-7-4-10-39(19)26(48)18(14-40)38-24(46)17(11-22(43)44)36-21(42)13-34-23(45)15(35-20(41)12-30)6-3-9-33-28(31)32/h15-19,40H,1-14,29-30H2,(H,34,45)(H,35,41)(H,36,42)(H,37,47)(H,38,46)(H,43,44)(H,49,50)(H4,31,32,33)/t15-,16-,17-,18-,19-/m0/s1
InChI key   ZRVZOBGMZWVJOS-VMXHOPILSA-N
Gene Information   human ... ITGA2B(3674), ITGAV(3685)

Description

Amino Acid Sequence

Gly-Arg-Gly-Asp-Ser-Pro-Lys

General description

Gly-Arg-Gly-Asp-Ser-Pro-Lys is a RGD peptide. Naturally occurring RGD peptides, present in the ECM (extracellalar matrix) proteins, are involved in facilitating integrin-mediated cell adhesion to matrix proteins. RGD peptide is present as repeats in cell-adhesion protein, such as fibronectin and vitronectin. This tripeptide is recognized by cells by specific integrins (e.g. β1 , β3 , and β5 subunits), present on the cell surface and associated with the actin filament via the FA (focal adhesion)-complex.

Application

Gly-Arg-Gly-Asp-Ser-Pro-Lys (RGD peptide) has been used-
• as a blocking peptide to inhibit integrin-fibronectin binding
• in adhesion assay performed on porcine trophectoderm to study the influence of TGFβ (transforming growth factor) on cell adhesion
• for incubation of MC3T3-E1 osteoblast cells to determine its effect on cell adhesion measured by AFM (atomic force microscopy)
• for the preparation of RGD.Flt23k.NR nanoparticles
• to determine the involvement of RGD-integrin bonding in cell adhesion process

Biochem/physiol Actions

Fibronectin analog that binds to integrins.

Safety & Documentation

Safety Information

Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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