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
Abbreviations	RGD Peptide
ChEMBL	ChEMBL313763
ChemSpider	2575945 94603
Jmol interactive 3D	Image
MeSH	arginyl-glycyl-aspartic+acid
PubChem	3328704 104802
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	346.34 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).
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Infobox references

Arginylglycylaspartic acid (RGD) is a tripeptide composed of L-arginine, glycine, and L-aspartic acid. The sequence is a common element in cellular recognition.^[1] Arginylglycylaspartic acid is used as a biochemical tool in the study of this recognition.

RGD-peptides are implicated in cellular attachment via integrins, and can be used to coat synthetic scaffolds in tissue engineering to enhance cellular attachment by mimicking in vivo conditions.^[2]

References

1. Ruoslahti, Erkki; Pierschbacher, Michael D. (1986). "Arg-Gly-Asp: a versatile cell recognition signal". Cell 44 (4): 517–18. doi:10.1016/0092-8674(86)90259-X. PMID 2418980.
2. Jeschke, B; Meyer, J; Jonczyk, A; Kessler, H; Adamietz, P; Meenen, NM; Kantlehner, M; Goepfert, C; Nies, B (2002). "RGD-peptides for tissue engineering of articular cartilage". Biomaterials 23 (16): 3455–63. doi:10.1016/s0142-9612(02)00052-2. PMID 12099289.