MedKoo Cat#: 597536 | Name: Myristoyl tripeptide-1

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Myristoyl tripeptide-1 is a peptide.

Chemical Structure

Myristoyl tripeptide-1
Myristoyl tripeptide-1
CAS#748816-12-8

Theoretical Analysis

MedKoo Cat#: 597536

Name: Myristoyl tripeptide-1

CAS#: 748816-12-8

Chemical Formula: C28H50N6O5

Exact Mass: 550.3843

Molecular Weight: 550.74

Elemental Analysis: C, 61.06; H, 9.15; N, 15.26; O, 14.52

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
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Synonym
Myristoyl tripeptide-1;
IUPAC/Chemical Name
tetradecanoylglycyl-L-histidyl-L-lysine
InChi Key
VXBPJKVVVMDBGY-ZEQRLZLVSA-N
InChi Code
InChI=1S/C28H50N6O5/c1-2-3-4-5-6-7-8-9-10-11-12-16-25(35)31-20-26(36)33-24(18-22-19-30-21-32-22)27(37)34-23(28(38)39)15-13-14-17-29/h19,21,23-24H,2-18,20,29H2,1H3,(H,30,32)(H,31,35)(H,33,36)(H,34,37)(H,38,39)/t23-,24-/m0/s1
SMILES Code
NCCCC[C@@H](C(O)=O)NC([C@H](CC1=CNC=N1)NC(CNC(CCCCCCCCCCCCC)=O)=O)=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 550.74 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Baksheeva VE, Nazipova AA, Zinchenko DV, Serebryakova MV, Senin II, Permyakov SE, Philippov PP, Li Y, Zamyatnin AA, Zernii EY, Aliev G. Ca2+ -myristoyl switch in neuronal calcium sensor-1: a role of C-terminal segment. CNS Neurol Disord Drug Targets. 2015;14(4):437-51. PubMed PMID: 25714968. 2: Jones JW, Lue L, Saiani A, Tiddy GJ. Density, DSC, X-ray and NMR measurements through the gel and lamellar phase transitions of 1-myristoyl-2-stearoyl-sn-glycero-3-phosphatidylcholine (MSPC) and 1-stearoyl-2-myristoyl-sn-glycero-3-phosphatidylcholine (SMPC): observation of slow relaxation processes and mechanisms of phase transitions. Phys Chem Chem Phys. 2012 Apr 28;14(16):5452-69. doi: 10.1039/c2cp23136k. Epub 2012 Mar 13. PubMed PMID: 22414900. 3: Colquhoun DR, Lyashkov AE, Ubaida Mohien C, Aquino VN, Bullock BT, Dinglasan RR, Agnew BJ, Graham DR. Bioorthogonal mimetics of palmitoyl-CoA and myristoyl-CoA and their subsequent isolation by click chemistry and characterization by mass spectrometry reveal novel acylated host-proteins modified by HIV-1 infection. Proteomics. 2015 Jun;15(12):2066-77. doi: 10.1002/pmic.201500063. Epub 2015 May 26. PubMed PMID: 25914232. 4: Vlach J, Saad JS. Trio engagement via plasma membrane phospholipids and the myristoyl moiety governs HIV-1 matrix binding to bilayers. Proc Natl Acad Sci U S A. 2013 Feb 26;110(9):3525-30. doi: 10.1073/pnas.1216655110. Epub 2013 Feb 11. PubMed PMID: 23401539; PubMed Central PMCID: PMC3587261. 5: Peshenko IV, Olshevskaya EV, Lim S, Ames JB, Dizhoor AM. Calcium-myristoyl Tug is a new mechanism for intramolecular tuning of calcium sensitivity and target enzyme interaction for guanylyl cyclase-activating protein 1: dynamic connection between N-fatty acyl group and EF-hand controls calcium sensitivity. J Biol Chem. 2012 Apr 20;287(17):13972-84. doi: 10.1074/jbc.M112.341883. Epub 2012 Mar 1. PubMed PMID: 22383530; PubMed Central PMCID: PMC3340203. 6: Li C, Lim S, Braunewell KH, Ames JB. Structure and Calcium Binding Properties of a Neuronal Calcium-Myristoyl Switch Protein, Visinin-Like Protein 3. PLoS One. 2016 Nov 7;11(11):e0165921. doi: 10.1371/journal.pone.0165921. eCollection 2016. PubMed PMID: 27820860; PubMed Central PMCID: PMC5098827. 7: Tove SB, Sutherland-Smith M. Toxicity of rac-1(3)-myristoyl glycerol to mice. J Nutr. 1988 Dec;118(12):1463-9. PubMed PMID: 3210075. 8: Lim S, Strahl T, Thorner J, Ames JB. Structure of a Ca2+-myristoyl switch protein that controls activation of a phosphatidylinositol 4-kinase in fission yeast. J Biol Chem. 2011 Apr 8;286(14):12565-77. doi: 10.1074/jbc.M110.208868. Epub 2011 Feb 2. PubMed PMID: 21288895; PubMed Central PMCID: PMC3069458. 9: Hwang JY, Koch KW. Calcium- and myristoyl-dependent properties of guanylate cyclase-activating protein-1 and protein-2. Biochemistry. 2002 Oct 29;41(43):13021-8. PubMed PMID: 12390029. 10: O'Callaghan DW, Burgoyne RD. Identification of residues that determine the absence of a Ca(2+)/myristoyl switch in neuronal calcium sensor-1. J Biol Chem. 2004 Apr 2;279(14):14347-54. Epub 2004 Jan 15. PubMed PMID: 14726528. 11: Xu X, Ishima R, Ames JB. Conformational dynamics of recoverin's Ca2+-myristoyl switch probed by 15N NMR relaxation dispersion and chemical shift analysis. Proteins. 2011 Jun;79(6):1910-22. doi: 10.1002/prot.23014. Epub 2011 Apr 4. PubMed PMID: 21465563; PubMed Central PMCID: PMC3092842. 12: Zheng GQ, Hu X, Cassady JM, Paige LA, Geahlen RL. Synthesis of myristoyl CoA analogues and myristoyl peptides as inhibitors of myristoyl CoA:protein N-myristoyltransferase. J Pharm Sci. 1994 Feb;83(2):233-8. PubMed PMID: 8169796. 13: Lim S, Dizhoor AM, Ames JB. Structural diversity of neuronal calcium sensor proteins and insights for activation of retinal guanylyl cyclase by GCAP1. Front Mol Neurosci. 2014 Mar 17;7:19. doi: 10.3389/fnmol.2014.00019. eCollection 2014. Review. PubMed PMID: 24672427; PubMed Central PMCID: PMC3956117. 14: Calvez P, Schmidt TF, Cantin L, Klinker K, Salesse C. Phosphatidylserine Allows Observation of the Calcium-Myristoyl Switch of Recoverin and Its Preferential Binding. J Am Chem Soc. 2016 Oct 11. [Epub ahead of print] PubMed PMID: 27689444. 15: Zhao C, Anand R, Braunewell KH. Nicotine-induced Ca2+-myristoyl switch of neuronal Ca2+ sensor VILIP-1 in hippocampal neurons: a possible crosstalk mechanism for nicotinic receptors. Cell Mol Neurobiol. 2009 Mar;29(2):273-86. doi: 10.1007/s10571-008-9320-z. Epub 2008 Oct 17. PubMed PMID: 18925431. 16: Renna L, Stefano G, Majeran W, Micalella C, Meinnel T, Giglione C, Brandizzi F. Golgi traffic and integrity depend on N-myristoyl transferase-1 in Arabidopsis. Plant Cell. 2013 May;25(5):1756-73. doi: 10.1105/tpc.113.111393. Epub 2013 May 14. PubMed PMID: 23673980; PubMed Central PMCID: PMC3694704. 17: Margetić A, Nannemann D, Meiler J, Huster D, Theisgen S. Guanylate Cyclase-Activating Protein-2 Undergoes Structural Changes upon Binding to Detergent Micelles and Bicelles. Biochim Biophys Acta. 2014 Nov;1838(11):2767-77. doi: 10.1016/j.bbamem.2014.07.012. Epub 2014 Jul 19. PubMed PMID: 25051529. 18: Kodali DR, Atkinson D, Small DM. Polymorphic behavior of 1,2-dipalmitoyl-3-lauroyl(PP12)- and 3-myristoyl(PP14)-sn-glycerols. J Lipid Res. 1990 Oct;31(10):1853-64. PubMed PMID: 2079608. 19: Raju RV, Sharma RK. Demonstration and purification of a myristoyl-CoA binding protein from bovine cardiac muscle. Life Sci. 1997;60(23):2145-53. PubMed PMID: 9180369. 20: Ames JB, Ishima R, Tanaka T, Gordon JI, Stryer L, Ikura M. Molecular mechanics of calcium-myristoyl switches. Nature. 1997 Sep 11;389(6647):198-202. PubMed PMID: 9296500.