Tetrapeptide-5

• CAT Number: I037151
• CAS Number: 883220-97-1
• Molecular Formula: C18H26N8O6
• Molecular Weight: 450.45
• Purity: 98%
• Synonyms: Tetrapeptide-5; beta-Ala-his-seryl-hist
• 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: (3-aminopropanoyl)-L-histidyl-L-seryl-L-histidine
• InChI: InChI=1S/C18H26N8O6/c19-2-1-15(28)24-12(3-10-5-20-8-22-10)16(29)26-14(7-27)17(30)25-13(18(31)32)4-11-6-21-9-23-11/h5-6,8-9,12-14,27H,1-4,7,19H2,(H,20,22)(H,21,23)(H,24,28)(H,25,30)(H,26,29)(H,31,32)/t12-,13-,14-/m0/s1
• InChIKey: QTEWJFPLRGWOOU-IHRRRGAJSA-N
• SMILES: O=C(O)[C@H](CC1=CNC=N1)NC([C@H](CO)NC([C@H](CC2=CNC=N2)NC(CCN)=O)=O)=O

Tetrapeptide-5 is a known humectant or hydroscopic moisturizer.

Reference

1: Ivanova EA, Sarycheva NY, Dubynin VA, Malyshev AV, Kalikhevich VN, Ardemasova ZA, Kamensky AA. Behavioral effects of original tetrapeptide, an analog of N-terminal nociceptin fragment. Bull Exp Biol Med. 2012 Jun;153(2):177-81. English, Russian. PubMed PMID: 22816077.
2: Izquierdo S, Kogan MJ, Parella T, Moglioni AG, Branchadell V, Giralt E, Ortuño RM. 14-helical folding in a cyclobutane-containing beta-tetrapeptide. J Org Chem. 2004 Jul 23;69(15):5093-9. PubMed PMID: 15255742.
3: Yang D, Qu J, Li W, Wang DP, Ren Y, Wu YD. A reverse turn structure induced by a D,L-alpha-aminoxy acid dimer. J Am Chem Soc. 2003 Nov 26;125(47):14452-7. PubMed PMID: 14624594.
4: Sibella-Argüelles C. The proliferation of human T lymphoblastic cells induced by 5-HT1B receptors activation is regulated by 5-HT-moduline. C R Acad Sci III. 2001 Apr;324(4):365-72. PubMed PMID: 11386084.
5: Seguin L, Seznec JC, Fillion G. The endogenous cerebral tetrapeptide 5-HT-moduline reduces in vivo the functional activity of central 5-HT1B receptors in the rat. Neurosci Res. 1997 Mar;27(3):277-80. PubMed PMID: 9129186.
6: Amoscato AA, Balasubramaniam A, Alexander JW, Babcock GF. Degradation of thymopentin by human lymphocytes: evidence for aminopeptidase activity. Biochim Biophys Acta. 1988 Jul 20;955(2):164-74. PubMed PMID: 3293664.
7: Rich DH, Jasensky RD, Mueller GC, Anderson KE. Analogues of the cytostatic cyclic tetrapeptide chlamydocin. Synthesis of N beta-(N-maleoylglycyl) and N beta-(tert-butyloxycarbonyl) derivatives of cyclo(Gly-L-Phe-D-Pro-L-Dap). J Med Chem. 1981 May;24(5):567-72. PubMed PMID: 7241514.