MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 597915 | Name: Pentapeptide-4

Description:

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

Pentapeptide-4 is a matrikine used in anti-wrinkle cosmetics.

Chemical Structure

Pentapeptide-4
Pentapeptide-4
CAS#149128-48-3

Theoretical Analysis

MedKoo Cat#: 597915

Name: Pentapeptide-4

CAS#: 149128-48-3

Chemical Formula: C23H45N7O9

Exact Mass: 563.3279

Molecular Weight: 563.65

Elemental Analysis: C, 49.01; H, 8.05; N, 17.40; O, 25.55

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.
Bulk Inquiry
Related CAS #
No Data
Synonym
Pentapeptide-4;
IUPAC/Chemical Name
L-lysyl-L-threonyl-L-threonyl-L-lysyl-L-serine
InChi Key
LDWBQGACJJOIKA-RHEFHGCGSA-N
InChi Code
InChI=1S/C23H45N7O9/c1-12(32)17(30-22(37)18(13(2)33)29-19(34)14(26)7-3-5-9-24)21(36)27-15(8-4-6-10-25)20(35)28-16(11-31)23(38)39/h12-18,31-33H,3-11,24-26H2,1-2H3,(H,27,36)(H,28,35)(H,29,34)(H,30,37)(H,38,39)/t12-,13-,14+,15+,16+,17+,18+/m1/s1
SMILES Code
OC[C@@H](C(O)=O)NC([C@H](CCCCN)NC([C@H]([C@H](O)C)NC([C@H]([C@H](O)C)NC([C@H](CCCCN)N)=O)=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 563.65 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: Vadlamani G, Thomas MD, Patel TR, Donald LJ, Reeve TM, Stetefeld J, Standing KG, Vocadlo DJ, Mark BL. The β-lactamase gene regulator AmpR is a tetramer that recognizes and binds the D-Ala-D-Ala motif of its repressor UDP-N-acetylmuramic acid (MurNAc)-pentapeptide. J Biol Chem. 2015 Jan 30;290(5):2630-43. doi: 10.1074/jbc.M114.618199. Epub 2014 Dec 5. PubMed PMID: 25480792; PubMed Central PMCID: PMC4316999. 2: Shah S, Heddle JG. Squaring up to DNA: pentapeptide repeat proteins and DNA mimicry. Appl Microbiol Biotechnol. 2014 Dec;98(23):9545-60. doi: 10.1007/s00253-014-6151-3. Epub 2014 Oct 26. Review. PubMed PMID: 25343976. 3: Warholm P, Light S. Identification of a Non-Pentapeptide Region Associated with Rapid Mycobacterial Evolution. PLoS One. 2016 May 5;11(5):e0154059. doi: 10.1371/journal.pone.0154059. eCollection 2016. PubMed PMID: 27149271; PubMed Central PMCID: PMC4858275. 4: Tomas E, Stanojevic V, McManus K, Khatri A, Everill P, Bachovchin WW, Habener JF. GLP-1(32-36)amide Pentapeptide Increases Basal Energy Expenditure and Inhibits Weight Gain in Obese Mice. Diabetes. 2015 Jul;64(7):2409-19. doi: 10.2337/db14-1708. Epub 2015 Apr 9. PubMed PMID: 25858562; PubMed Central PMCID: PMC4477344. 5: Tsiolaki PL, Hamodrakas SJ, Iconomidou VA. The pentapeptide LQVVR plays a pivotal role in human cystatin C fibrillization. FEBS Lett. 2015 Jan 2;589(1):159-64. doi: 10.1016/j.febslet.2014.11.041. Epub 2014 Dec 3. PubMed PMID: 25479090. 6: García-Fontana C, Corral Lugo A, Krell T. Specificity of the CheR2 methyltransferase in Pseudomonas aeruginosa is directed by a C-terminal pentapeptide in the McpB chemoreceptor. Sci Signal. 2014 Apr 8;7(320):ra34. doi: 10.1126/scisignal.2004849. PubMed PMID: 24714571. 7: Nakamura Y, Hayakawa A, Ishizawa H, Kamei Y, Tanaka S, Onda K, Sugiyama K, Hirano T. Immunomodulatory effects of the pentapeptide YGSRS on human peripheral-blood mononuclear cells. Immunopharmacol Immunotoxicol. 2015 Jun;37(3):318-23. doi: 10.3109/08923973.2015.1038752. Epub 2015 May 15. PubMed PMID: 25975580. 8: Elahi D, Angeli FS, Vakilipour A, Carlson OD, Tomas E, Egan JM, Habener JF, Shannon RP. GLP-1(32-36)amide, a novel pentapeptide cleavage product of GLP-1, modulates whole body glucose metabolism in dogs. Peptides. 2014 Sep;59:20-4. doi: 10.1016/j.peptides.2014.06.004. Epub 2014 Jun 14. PubMed PMID: 24937653; PubMed Central PMCID: PMC5155305. 9: Sridhar S, Nagamruta M, Guruprasad K. Analyses of the Sequence and Structural Properties Corresponding to Pentapeptide and Large Palindromes in Proteins. PLoS One. 2015 Oct 14;10(10):e0139568. doi: 10.1371/journal.pone.0139568. eCollection 2015. PubMed PMID: 26465610; PubMed Central PMCID: PMC4605511. 10: Oishi S, Kuroyanagi T, Kubo T, Montpas N, Yoshikawa Y, Misu R, Kobayashi Y, Ohno H, Heveker N, Furuya T, Fujii N. Development of novel CXC chemokine receptor 7 (CXCR7) ligands: selectivity switch from CXCR4 antagonists with a cyclic pentapeptide scaffold. J Med Chem. 2015 Jul 9;58(13):5218-25. doi: 10.1021/acs.jmedchem.5b00216. Epub 2015 Jun 18. PubMed PMID: 26042340. 11: Batra M, Sharma R, Malik A, Dhindwal S, Kumar P, Tomar S. Crystal structure of pentapeptide-independent chemotaxis receptor methyltransferase (CheR) reveals idiosyncratic structural determinants for receptor recognition. J Struct Biol. 2016 Dec;196(3):364-374. doi: 10.1016/j.jsb.2016.08.005. Epub 2016 Aug 17. PubMed PMID: 27544050. 12: Kolodkin-Gal I, Hazan R, Gaathon A, Carmeli S, Engelberg-Kulka H. A linear pentapeptide is a quorum-sensing factor required for mazEF-mediated cell death in Escherichia coli. Science. 2007 Oct 26;318(5850):652-5. PubMed PMID: 17962566. 13: Rohokale RS, Dhavale DD. Synthesis of (2S,3R)-3-amino-2-hydroxydecanoic acid and its enantiomer: a non-proteinogenic amino acid segment of the linear pentapeptide microginin. Beilstein J Org Chem. 2014 Mar 17;10:667-71. doi: 10.3762/bjoc.10.59. eCollection 2014. PubMed PMID: 24778718; PubMed Central PMCID: PMC3999816. 14: Sato A, Suzuki T, Oikawa K, Ohta R, Ebina K. An endothelin-3-related synthetic biotinylated pentapeptide as a novel inhibitor of platelet-activating factor. Eur J Pharmacol. 2013 Aug 15;714(1-3):142-7. doi: 10.1016/j.ejphar.2013.05.050. Epub 2013 Jun 19. PubMed PMID: 23792041. 15: Lunagariya J, Zhong S, Chen J, Bai D, Bhadja P, Long W, Liao X, Tang X, Xu S. Design and Synthesis of Analogues of Marine Natural Product Galaxamide, an N-methylated Cyclic Pentapeptide, as Potential Anti-Tumor Agent in Vitro. Mar Drugs. 2016 Sep 3;14(9). pii: E161. doi: 10.3390/md14090161. PubMed PMID: 27598177; PubMed Central PMCID: PMC5039532. 16: Gibello A, Díaz de Alba P, Blanco MM, Machuca J, Cutuli MT, Rodríguez-Martínez JM. Lactococcus garvieae carries a chromosomally encoded pentapeptide repeat protein that confers reduced susceptibility to quinolones in Escherichia coli producing a cytotoxic effect. Res Microbiol. 2014 Sep;165(7):590-9. doi: 10.1016/j.resmic.2014.05.033. Epub 2014 Jun 3. PubMed PMID: 24965125. 17: Pravdivtsev AN, Yurkovskaya AV, Vieth HM, Ivanov KL. High resolution NMR study of T₁ magnetic relaxation dispersion. IV. Proton relaxation in amino acids and Met-enkephalin pentapeptide. J Chem Phys. 2014 Oct 21;141(15):155101. doi: 10.1063/1.4897336. PubMed PMID: 25338911. 18: Go HJ, Kim CH, Oh HY, Park NG. Novel pentapeptide, PALAL, derived from a bony fish elicits contraction of the muscle in starfish Patiria pectinifera. J Pept Sci. 2016 Oct;22(10):628-635. doi: 10.1002/psc.2911. Epub 2016 Aug 10. PubMed PMID: 27506561. 19: Bortolus M, Wright K, Toffoletti A, Toniolo C, Maniero AL. Self-association of an enantiopure β-pentapeptide in nematic liquid crystals. Chemistry. 2013 Dec 23;19(52):17963-8. doi: 10.1002/chem.201303000. Epub 2013 Nov 15. PubMed PMID: 24243483. 20: Chang J, Zhou H, Preobrazhenskaya M, Tao P, Kim SJ. Correction to The Carboxyl Terminus of Eremomycin Facilitates Binding to the Non-d-Ala-d-Ala Segment of the Peptidoglycan Pentapeptide Stem. Biochemistry. 2016 Jul 19;55(28):4003. doi: 10.1021/acs.biochem.6b00643. Epub 2016 Jul 6. PubMed PMID: 27383460.