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

Hodoodo CAT#: H597541

CAS#: 19431-21-1

Description: Pentalysine is a peptide.


Chemical Structure

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Pentalysine
CAS# 19431-21-1

Theoretical Analysis

Hodoodo Cat#: H597541
Name: Pentalysine
CAS#: 19431-21-1
Chemical Formula: C30H62N10O6
Exact Mass: 658.49
Molecular Weight: 658.890
Elemental Analysis: C, 54.69; H, 9.49; N, 21.26; O, 14.57

Price and Availability

Size Price Availability Quantity
10mg USD 300
50mg USD 630
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Synonym: Pentalysine; Lys-lys-lys-lys-lys;

IUPAC/Chemical Name: L-lysyl-L-lysyl-L-lysyl-L-lysyl-L-lysine

InChi Key: IXPHOHNWDLRFJH-KEOOTSPTSA-N

InChi Code: InChI=1S/C30H62N10O6/c31-16-6-1-11-21(36)26(41)37-22(12-2-7-17-32)27(42)38-23(13-3-8-18-33)28(43)39-24(14-4-9-19-34)29(44)40-25(30(45)46)15-5-10-20-35/h21-25H,1-20,31-36H2,(H,37,41)(H,38,42)(H,39,43)(H,40,44)(H,45,46)/t21-,22-,23-,24-,25-/m0/s1

SMILES Code: NCCCC[C@@H](C(O)=O)NC([C@H](CCCCN)NC([C@H](CCCCN)NC([C@H](CCCCN)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:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 658.89 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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Poulsen N, Scheffel A, Sheppard VC, Chesley PM, Kröger N. Pentalysine clusters mediate silica targeting of silaffins in Thalassiosira pseudonana. J Biol Chem. 2013 Jul 12;288(28):20100-9. doi: 10.1074/jbc.M113.469379. Epub 2013 May 17. PubMed PMID: 23720751; PubMed Central PMCID: PMC3711277.

2: Geiger Y, Gottlieb HE, Akbey Ü, Oschkinat H, Goobes G. Studying the Conformation of a Silaffin-Derived Pentalysine Peptide Embedded in Bioinspired Silica using Solution and Dynamic Nuclear Polarization Magic-Angle Spinning NMR. J Am Chem Soc. 2016 May 4;138(17):5561-7. doi: 10.1021/jacs.5b07809. Epub 2016 Apr 20. PubMed PMID: 26451953.

3: Chen Z, Zhou S, Chen J, Deng Y, Luo Z, Chen H, Hamblin MR, Huang M. Pentalysine beta-carbonylphthalocyanine zinc: an effective tumor-targeting photosensitizer for photodynamic therapy. ChemMedChem. 2010 Jun 7;5(6):890-8. doi: 10.1002/cmdc.201000042. PubMed PMID: 20458713; PubMed Central PMCID: PMC2935799.

4: Lohman TM, deHaseth PL, Record MT Jr. Pentalysine-deoxyribonucleic acid interactions: a model for the general effects of ion concentrations on the interactions of proteins with nucleic acids. Biochemistry. 1980 Jul 22;19(15):3522-30. PubMed PMID: 7407056.

5: Roux M, Neumann JM, Bloom M, Devaux PF. 2H and 31P NMR study of pentalysine interaction with headgroup deuterated phosphatidylcholine and phosphatidylserine. Eur Biophys J. 1988;16(5):267-73. PubMed PMID: 3240757.

6: Breitenkamp RB, Emrick T. Pentalysine-grafted ROMP polymers for DNA complexation and delivery. Biomacromolecules. 2008 Sep;9(9):2495-500. doi: 10.1021/bm800511p. Epub 2008 Jul 30. PubMed PMID: 18665641.

7: Zhang H, Grabenauer M, Bowers MT, Dearden DV. Supramolecular modification of ion chemistry: modulation of peptide charge state and dissociation behavior through complexation with cucurbit[n]uril (n = 5, 6) or alpha-cyclodextrin. J Phys Chem A. 2009 Feb 26;113(8):1508-17. doi: 10.1021/jp808625v. Epub 2009 Feb 3. PubMed PMID: 19191519.

8: Carroll D, Botchan MR. Competition between pentalysine and actinomycin D for binding to DNA. Biochem Biophys Res Commun. 1972 Feb 25;46(4):1661-7. PubMed PMID: 5062742.

9: Rehan M, Sagar A, Sharma V, Mishra S, Ashish, Sahni G. Penta-L-lysine Potentiates Fibrin-Independent Activity of Human Tissue Plasminogen Activator. J Phys Chem B. 2015 Oct 22;119(42):13271-7. doi: 10.1021/acs.jpcb.5b07735. Epub 2015 Oct 8. PubMed PMID: 26447340.

10: Braun KP, Cody RB Jr, Jones DR, Peterson CM. A structural assignment for a stable acetaldehyde-lysine adduct. J Biol Chem. 1995 May 12;270(19):11263-6. PubMed PMID: 7744761.

11: Shannon TR, Hale CC, Milanick MA. Interaction of cardiac Na-Ca exchanger and exchange inhibitory peptide with membrane phospholipids. Am J Physiol. 1994 May;266(5 Pt 1):C1350-6. PubMed PMID: 8203499.

12: Kleinschmidt JH, Marsh D. Spin-label electron spin resonance studies on the interactions of lysine peptides with phospholipid membranes. Biophys J. 1997 Nov;73(5):2546-55. PubMed PMID: 9370448; PubMed Central PMCID: PMC1181156.

13: Newton GL, Ly A, Tran NQ, Ward JF, Milligan JR. Radioprotection of plasmid DNA by oligolysines. Int J Radiat Biol. 2004 Sep;80(9):643-51. PubMed PMID: 15586884.

14: Mosior M, McLaughlin S. Electrostatics and reduction of dimensionality produce apparent cooperativity when basic peptides bind to acidic lipids in membranes. Biochim Biophys Acta. 1992 Mar 23;1105(1):185-7. PubMed PMID: 1567895.

15: Rovaldi CR, Pievsky A, Sole NA, Friden PM, Rothstein DM, Spacciapoli P. Photoactive porphyrin derivative with broad-spectrum activity against oral pathogens In vitro. Antimicrob Agents Chemother. 2000 Dec;44(12):3364-7. PubMed PMID: 11083641; PubMed Central PMCID: PMC90206.

16: Kakinoki S, Sakai Y, Fujisato T, Yamaoka T. Accelerated tissue integration into porous materials by immobilizing basic fibroblast growth factor using a biologically safe three-step reaction. J Biomed Mater Res A. 2015 Dec;103(12):3790-7. doi: 10.1002/jbm.a.35516. Epub 2015 Jun 29. PubMed PMID: 26034014.

17: Schott H, Eckstein H. [Determination of the interaction of oligopeptides and oligonucleotides by a chromatographic technique (author's transl)]. Hoppe Seylers Z Physiol Chem. 1979 Nov;360(11):1689-92. German. PubMed PMID: 511103.

18: Wu J, Zawistowski A, Ehrmann M, Yi T, Schmuck C. Peptide functionalized polydiacetylene liposomes act as a fluorescent turn-on sensor for bacterial lipopolysaccharide. J Am Chem Soc. 2011 Jun 29;133(25):9720-3. doi: 10.1021/ja204013u. Epub 2011 May 31. PubMed PMID: 21615123.

19: Mihajlovic M, Lazaridis T. Calculations of pH-dependent binding of proteins to biological membranes. J Phys Chem B. 2006 Feb 23;110(7):3375-84. PubMed PMID: 16494352.

20: Soto-Cruz I, Magee AI. Effect of synthetic peptides representing the hypervariable region of p21ras on Xenopus laevis oocyte maturation. Biochem J. 1995 Feb 15;306 ( Pt 1):11-4. PubMed PMID: 7864796; PubMed Central PMCID: PMC1136474.