Arginylglycylaspartic acid

Arginylglycylaspartic acid
Names
	Systematic IUPAC name (2S)-2-[[2-[[(2S)-2-amino-5-(diaminomethylideneamino)pentanoyl]amino]acetyl]amino]butanedioic acid
	Other names L-Arginyl-Glycyl-L-Aspartic acid; Arg-Gly-Asp
Identifiers
CAS Number	99896-85-2 ;
3D model (JSmol)	Interactive image;
Abbreviations	RGD Peptide[citation needed]
ChEMBL	ChEMBL313763 ;
ChemSpider	2575945 ; 94603 ;
MeSH	arginyl-glycyl-aspartic+acid
PubChem CID	3328704; 104802;
UNII	78VO7F77PN ;
CompTox Dashboard (EPA)	DTXSID30912420 ;
	InChI InChI=1S/C12H22N6O6/c13-6(2-1-3-16-12(14)15)10(22)17-5-8(19)18-7(11(23)24)4-9(20)21/h6-7H,1-5,13H2,(H,17,22)(H,18,19)(H,20,21)(H,23,24)(H4,14,15,16) Key: IYMAXBFPHPZYIK-UHFFFAOYSA-N ;
	SMILES C(C[C@@H](C(=O)NCC(=O)N[C@@H](CC(=O)O)C(=O)O)N)CN=C(N)N;
Properties
Chemical formula	C12H22N6O6
Molar mass	346.344 g·mol−1
log P	−3.016
Acidity (pKa)	2.851
Basicity (pKb)	11.146
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Arginylglycylaspartic acid (RGD) is the most common peptide motif responsible for cell adhesion to the extracellular matrix (ECM), found in species ranging from Drosophila to humans. Cell adhesion proteins called integrins recognize and bind to this sequence, which is found within many matrix proteins, including fibronectin, fibrinogen, vitronectin, osteopontin, and several other adhesive extracellular matrix proteins.^[1] The discovery of RGD and elucidation of how RGD binds to integrins has led to the development of a number of drugs and diagnostics,^[2] while the peptide itself is used ubiquitously in bioengineering.^[3] Depending on the application and the integrin targeted, RGD can be chemically modified or replaced by a similar peptide which promotes cell adhesion.

^ Plow, Edward F.; Haas, Thomas A.; Zhang, Li; Loftus, Joseph; Smith, Jeffrey W. (2000-07-21). "Ligand Binding to Integrins". Journal of Biological Chemistry. 275 (29): 21785–21788. doi:10.1074/jbc.R000003200. ISSN 0021-9258. PMID 10801897.
^ Cite error: The named reference :11 was invoked but never defined (see the help page).
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[:14-1] Plow, Edward F.; Haas, Thomas A.; Zhang, Li; Loftus, Joseph; Smith, Jeffrey W. (2000-07-21). "Ligand Binding to Integrins". Journal of Biological Chemistry. 275 (29): 21785–21788. doi:10.1074/jbc.R000003200. ISSN 0021-9258. PMID 10801897.

[:11-2] Cite error: The named reference :11 was invoked but never defined (see the help page).

[:6-3] Cite error: The named reference :6 was invoked but never defined (see the help page).

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