Tyrosyl-glycyl-glycine

• CAT Number: I037671
• CAS Number: 21778-69-8
• Molecular Formula: C13H17N3O5
• Molecular Weight: 295.295
• Purity: 98%
• Synonyms: Tyrosyl-glycyl-glycine
• Solubility: Soluble in DMSO
• Appearance: Solid powder
• Storage: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
• IUPAC Name: Glycine, N-(N-L-tyrosylglycyl)-
• InChI: InChI=1S/C13H17N3O5/c14-10(5-8-1-3-9(17)4-2-8)13(21)16-6-11(18)15-7-12(19)20/h1-4,10,17H,5-7,14H2,(H,15,18)(H,16,21)(H,19,20)/t10-/m0/s1
• InChIKey: HIINQLBHPIQYHN-JTQLQIEISA-N
• SMILES: C(NCC(NCC(=O)O)=O)([C@H](Cc1ccc(O)cc1)N)=O

Tyrosyl-glycyl-glycine is a biochemical.

Reference

1: Furukawa S, Fukuyama T, Matsui A, Kuratsu M, Nakaya R, Ineyama T, Ueda H, Ryu I. Coupling-Reagent-Free Synthesis of Dipeptides and Tripeptides Using Amino Acid Ionic Liquids. Chemistry. 2015 Aug 17;21(34):11980-3. doi: 10.1002/chem.201501783. Epub 2015 Jul 17. PubMed PMID: 26213326.
2: Lai CK, Mu X, Hao Q, Hopkinson AC, Chu IK. Formation, isomerization, and dissociation of ε- and α-carbon-centered tyrosylglycylglycine radical cations. Phys Chem Chem Phys. 2014 Nov 28;16(44):24235-43. doi: 10.1039/c4cp03119a. PubMed PMID: 25293584.
3: Abo-Riziq A, Grace L, Crews B, Callahan MP, van Mourik T, de Vries MS. Conformational structure of tyrosine, tyrosyl-glycine, and tyrosyl-glycyl-glycine by double resonance spectroscopy. J Phys Chem A. 2011 Jun 16;115(23):6077-87. doi: 10.1021/jp110601w. Epub 2011 Mar 17. PubMed PMID: 21413771.
4: Afonine PV, Grosse-Kunstleve RW, Adams PD, Lunin VY, Urzhumtsev A. On macromolecular refinement at subatomic resolution with interatomic scatterers. Acta Crystallogr D Biol Crystallogr. 2007 Nov;63(Pt 11):1194-7. Epub 2007 Oct 17. PubMed PMID: 18007035; PubMed Central PMCID: PMC2808317.
5: Gong JR, Yan HJ, Yuan QH, Xu LP, Bo ZS, Wan LJ. Controllable distribution of single molecules and peptides within oligomer template investigated by STM. J Am Chem Soc. 2006 Sep 27;128(38):12384-5. PubMed PMID: 16984166.
6: Amini-Bavil-Olyaee S, Sarrami-Forooshani R, Adeli A, Mahboudi F, Sabahi F, Nafisi H, Zali MR, Azizi M. A novel accurate amplification created restriction site method for determination of the wild type and the precore mutant hepatitis B virus variants. J Virol Methods. 2005 Jul;127(1):19-23. Epub 2005 Apr 19. PubMed PMID: 15893561.
7: Jakas A, Horvat S. The effect of glycation on the chemical and enzymatic stability of the endogenous opioid peptide, leucine-enkephalin, and related fragments. Bioorg Chem. 2004 Dec;32(6):516-26. PubMed PMID: 15530992.
8: Varga-Defterdarović L, Hrlec G. Synthesis and intramolecular reactions of Tyr-Gly and Tyr-Gly-Gly related 6-O-glucopyranose esters. Carbohydr Res. 2004 Jan 2;339(1):67-75. PubMed PMID: 14659672.
9: Cristoni S, Bernardi LR, Biunno I, Guidugli F. Analysis of peptides using partial (no discharge) atmospheric pressure chemical ionization conditions with ion trap mass spectrometry. Rapid Commun Mass Spectrom. 2002;16(17):1686-91. PubMed PMID: 12203237.
10: Pichon-Pesme V, Lachekar H, Souhassou M, Lecomte C. Electron density and electrostatic properties of two peptide molecules: tyrosyl-glycyl-glycine monohydrate and glycyl-aspartic acid dihydrate. Acta Crystallogr B. 2000 Aug;56(Pt 4):728-37. PubMed PMID: 10944266.
11: Mizuma T, Sakai N, Hagi K, Awazu S. Transport and recognition of aminopeptidase-resistant cellobiose-coupled tyrosylglycylglycine by intestinal Na+/glucose cotransporter (SGLT1): recognition of sugar conjugates by SGLT1 is much less restricted than transport. Biol Pharm Bull. 1999 Aug;22(8):876-9. PubMed PMID: 10480331.
12: Zacharie B, Lagraoui M, Dimarco M, Penney CL, Gagnon L. Thioamides: synthesis, stability, and immunological activities of thioanalogues of Imreg. Preparation of new thioacylating agents using fluorobenzimidazolone derivatives. J Med Chem. 1999 Jun 3;42(11):2046-52. PubMed PMID: 10354413.
13: Nucaro E, Jodra M, Russell E, Anderson L, Dennison P, Dufton M. Conversion of tyrosine to phenolic derivatives by Taiwan cobra venom. Toxicon. 1998 Aug;36(8):1173-87. PubMed PMID: 9690784.
14: Haseto S, Mizuma T, Ouchi H, Isoda T, Hayashi M, Awazu S. Preference of Peyer’s patches to jejunal epithelium for intestinal absorption of oligopeptides, tyrosylglycylglycine and D-kyotorphin. Biol Pharm Bull. 1997 Sep;20(9):1024-5. PubMed PMID: 9331991.
15: Jain R, Freund HG, Budzinsky E, Sharma M. Radiation-induced formation of 3,4-dihydroxyphenylalanine in tyrosine-containing peptides and proteins as a function of X-irradiation dose. Bioconjug Chem. 1997 Mar-Apr;8(2):173-8. PubMed PMID: 9095357.
16: Armstrong K, Banerjee N, Ghilchick M, Reed MJ, Parish DC. Neutral endopeptidase activity in breast cysts. Biochem Soc Trans. 1996 Aug;24(3):337S. PubMed PMID: 8878881.
17: Kayser H, Meisel H. Stimulation of human peripheral blood lymphocytes by bioactive peptides derived from bovine milk proteins. FEBS Lett. 1996 Mar 25;383(1-2):18-20. PubMed PMID: 8612782.
18: Haberstock H, Marotti T. The relevance of intact enkephalin molecule in predominantly delta opioid receptor mediated superoxide anion release. Neuropeptides. 1995 Dec;29(6):357-65. PubMed PMID: 8837964.
19: Mizuma T, Sakai N, Awazu S. Na(+)-dependent transport of aminopeptidase-resistant sugar-coupled tripeptides in rat intestine. Biochem Biophys Res Commun. 1994 Sep 30;203(3):1412-6. PubMed PMID: 7945288.
20: Urbani A, Bongiorno L, Marini M, Bolacchi F, Zona C, Roda LG. Effect of differentiation on hydrolysis and association of Leu-enkephalin to K562(S) cells. Peptides. 1994;15(7):1213-22. PubMed PMID: 7854972.