G1269

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

≥97% (HPLC)

• Synonym(s): GRGDSPK
• Empirical Formula (Hill Notation): C₂₈H₄₉N₁₁O₁₁
• CAS Number: 111119-28-9
• Molecular Weight: 715.76
• MDL number: MFCD00076462
• UNSPSC Code: 12352209
• PubChem Substance ID: 24895055
• NACRES: NA.32

Properties

• biological source: human
• Quality Level: 200
• assay: ≥97% (HPLC)
• form: powder
• technique(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.[1] 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.[2]

Application

Gly-Arg-Gly-Asp-Ser-Pro-Lys (RGD peptide) has been used-

• as a blocking peptide to inhibit integrin-fibronectin binding[3]
• in adhesion assay performed on porcine trophectoderm to study the influence of TGFβ (transforming growth factor) on cell adhesion[4]
• for incubation of MC3T3-E1 osteoblast cells to determine its effect on cell adhesion measured by AFM (atomic force microscopy)[2]
• for the preparation of RGD.Flt23k.NR nanoparticles[5]
• to determine the involvement of RGD-integrin bonding in cell adhesion process[6]

Biochem/physiol Actions

Fibronectin analog that binds to integrins.

Safety Information

• 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)