Alanyltyrosine

• CAT Number: I021715
• CAS Number: 3061-88-9
• Molecular Formula: C12H16N2O4
• Molecular Weight: 252.27
• Purity: 98%
• Synonyms: Alanyltyrosine
• 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: L-alanyl-L-tyrosine
• InChI: InChI=1S/C12H16N2O4/c1-7(13)11(16)14-10(12(17)18)6-8-2-4-9(15)5-3-8/h2-5,7,10,15H,6,13H2,1H3,(H,14,16)(H,17,18)/t7-,10-/m0/s1
• InChIKey: ALZVPLKYDKJKQU-XVKPBYJWSA-N
• SMILES: OC1=CC=C(C=C1)C[C@@H](C(O)=O)NC([C@H](C)N)=O

Alanyltyrosine is a dipeptide composed of alanine and tyrosine. It is an incomplete breakdown product of protein digestion or protein catabolism. Some dipeptides are known to have physiological or cell-signaling effects although most are simply short-lived intermediates on their way to specific amino acid degradation pathways following further proteolysis.

Reference

1: Sawai H, Taira H, Ishibashi K, Itoh M. Synthesis and biological activities of beta-alanyltyrosine derivative of 2′,5′-oligoadenylate, and its use in radiobinding assay for 2′,5-oligoadenylate. J Biochem. 1987 Feb;101(2):339-46. PubMed PMID: 3584089.
2: Sawai H. Synthesis, properties and use of beta-alanyltyrosine derivatives of 2′,5′-oligoadenylate 5′-triphosphate. Nucleic Acids Symp Ser. 1985;(16):137-40. PubMed PMID: 3003702.
3: Liu S, Li Z, Conti PS. Development of multi-functional chelators based on sarcophagine cages. Molecules. 2014 Apr 3;19(4):4246-55. doi: 10.3390/molecules19044246. PubMed PMID: 24705567.
4: Zhou C, Hu J, Ma H, Yagoub AE, Yu X, Owusu J, Ma H, Qin X. Antioxidant peptides from corn gluten meal: Orthogonal design evaluation. Food Chem. 2015 Nov 15;187:270-8. doi: 10.1016/j.foodchem.2015.04.092. Epub 2015 Apr 23. PubMed PMID: 25977026.
5: Dearling JL, Paterson BM, Akurathi V, Betanzos-Lara S, Treves ST, Voss SD, White JM, Huston JS, Smith SV, Donnelly PS, Packard AB. The ionic charge of copper-64 complexes conjugated to an engineered antibody affects biodistribution. Bioconjug Chem. 2015 Apr 15;26(4):707-17. doi: 10.1021/acs.bioconjchem.5b00049. Epub 2015 Mar 12. PubMed PMID: 25719414.
6: Gourni E, Del Pozzo L, Kheirallah E, Smerling C, Waser B, Reubi JC, Paterson BM, Donnelly PS, Meyer PT, Maecke HR. Copper-64 Labeled Macrobicyclic Sarcophagine Coupled to a GRP Receptor Antagonist Shows Great Promise for PET Imaging of Prostate Cancer. Mol Pharm. 2015 Aug 3;12(8):2781-90. doi: 10.1021/mp500671j. Epub 2015 Jul 15. PubMed PMID: 26132879.
7: Chu W, Li X, Gao N, Deng Y, Yin D, Li D, Chu T. Peptide bonds affect the formation of haloacetamides, an emerging class of N-DBPs in drinking water: free amino acids versus oligopeptides. Sci Rep. 2015 Sep 23;5:14412. doi: 10.1038/srep14412. PubMed PMID: 26394759; PubMed Central PMCID: PMC4585778.
8: Zhang Z, Zhao Y, Wang X, Lin R, Zhang Y, Ma H, Guo Y, Xu L, Zhao B. The novel dipeptide Tyr-Ala (TA) significantly enhances the lifespan and healthspan of Caenorhabditis elegans. Food Funct. 2016 Apr;7(4):1975-84. doi: 10.1039/c5fo01302j. PubMed PMID: 26987062.
9: Macurkova A, Neubauerova T, Poncova K, Jezek R, Lovecka P, Spiwok V, Mackova M, Macek T. Effect of chain elongation on biological properties of the toxin paralysin β-alanyl-tyrosine. Chem Biol Drug Des. 2014 Apr;83(4):418-26. doi: 10.1111/cbdd.12257. PubMed PMID: 24168419.
10: Hooshyar Z, Rezanejade Bardajee G, Kakavand N, Khanjari M, Dianatnejad N. Investigations on the interactions of DiAmsar with serum albumins: Insights from spectroscopic and molecular docking techniques. Luminescence. 2015 Aug;30(5):538-48. doi: 10.1002/bio.2773. Epub 2014 Oct 14. PubMed PMID: 25311912.
11: Wu Z, Liu S, Nair I, Omori K, Scott S, Todorov I, Shively JE, Conti PS, Li Z, Kandeel F. (64)Cu labeled sarcophagine exendin-4 for microPET imaging of glucagon like peptide-1 receptor expression. Theranostics. 2014 May 24;4(8):770-7. doi: 10.7150/thno.7759. eCollection 2014. PubMed PMID: 24955138; PubMed Central PMCID: PMC4063975.
12: Pérez M, Wappner P, Quesada-Allué LA. Catecholamine-beta-alanyl ligase in the medfly Ceratitis capitata. Insect Biochem Mol Biol. 2002 Jun;32(6):617-25. PubMed PMID: 12020836.
13: Liu S, Li D, Huang CW, Yap LP, Park R, Shan H, Li Z, Conti PS. Efficient construction of PET/fluorescence probe based on sarcophagine cage: an opportunity to integrate diagnosis with treatment. Mol Imaging Biol. 2012 Dec;14(6):718-24. doi: 10.1007/s11307-012-0557-z. PubMed PMID: 22476968.
14: Ma MT, Neels OC, Denoyer D, Roselt P, Karas JA, Scanlon DB, White JM, Hicks RJ, Donnelly PS. Gallium-68 complex of a macrobicyclic cage amine chelator tethered to two integrin-targeting peptides for diagnostic tumor imaging. Bioconjug Chem. 2011 Oct 19;22(10):2093-103. doi: 10.1021/bc200319q. Epub 2011 Sep 27. PubMed PMID: 21877750.
15: Liu S, Li Z, Yap LP, Huang CW, Park R, Conti PS. Efficient preparation and biological evaluation of a novel multivalency bifunctional chelator for 64Cu radiopharmaceuticals. Chemistry. 2011 Sep 5;17(37):10222-5. doi: 10.1002/chem.201101894. Epub 2011 Aug 4. PubMed PMID: 21815227; PubMed Central PMCID: PMC5367772.
16: Schorlemmer HU, Opitz W, Etschenberg E, Bitter-Suermann D, Hadding U. Killing of tumor cells in vitro by macrophages from mice treated with synthetic dehydrodipeptides. Cancer Res. 1979 May;39(5):1847-53. PubMed PMID: 427817.
17: Svobodová J, Beneš M, Dubský P, Vigh G, Gaš B. Simulation of the effects of complex-formation equilibria in electrophoresis: III. Simultaneous effects of chiral selector concentration and background electrolyte pH. Electrophoresis. 2012 Oct;33(19-20):3012-20. doi: 10.1002/elps.201200293. Epub 2012 Sep 20. PubMed PMID: 22996563.
18: Wadas TJ, Wong EH, Weisman GR, Anderson CJ. Copper chelation chemistry and its role in copper radiopharmaceuticals. Curr Pharm Des. 2007;13(1):3-16. Review. PubMed PMID: 17266585.
19: Mu X, Song T, Xu M, Lai CK, Siu CK, Laskin J, Chu IK. Discovery and mechanistic studies of facile N-terminal Cα-C bond cleavages in the dissociation of tyrosine-containing peptide radical cations. J Phys Chem B. 2014 Apr 24;118(16):4273-81. doi: 10.1021/jp410525f. Epub 2014 Apr 15. PubMed PMID: 24678922.
20: Druml W, Hübl W, Roth E, Lochs H. Utilization of tyrosine-containing dipeptides and N-acetyl-tyrosine in hepatic failure. Hepatology. 1995 Apr;21(4):923-8. PubMed PMID: 7705801.