Lysyllysyllysine | CAS#13184-14-0 | cationic moietie

MedKoo Cat#: 597519 | Name: Lysyllysyllysine

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Description:

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

Lysyllysyllysine is a cationic moietie that may be used in the construction of gene delivery vectors and DNA nanoparticles.

Chemical Structure

Lysyllysyllysine

CAS#13184-14-0

Theoretical Analysis

MedKoo Cat#: 597519

Name: Lysyllysyllysine

CAS#: 13184-14-0

Chemical Formula: C18H38N6O4

Exact Mass: 402.2955

Molecular Weight: 402.54

Elemental Analysis: C, 53.71; H, 9.52; N, 20.88; O, 15.90

Price and Availability

Size	Price	Availability	Quantity
50mg	USD 485.00	2 Weeks

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Synonym

Lysyllysyllysine; Lys-lys-lys; Trilysine; L-Lysine, L-lysyl-L-lysyl-;

IUPAC/Chemical Name

L-lysyl-L-lysyl-L-lysine

InChi Key

WBSCNDJQPKSPII-KKUMJFAQSA-N

InChi Code

InChI=1S/C18H38N6O4/c19-10-4-1-7-13(22)16(25)23-14(8-2-5-11-20)17(26)24-15(18(27)28)9-3-6-12-21/h13-15H,1-12,19-22H2,(H,23,25)(H,24,26)(H,27,28)/t13-,14-,15-/m0/s1

SMILES Code

NCCCC[C@@H](C(O)=O)NC([C@H](CCCCN)NC([C@H](CCCCN)N)=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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Lysyllysyllysine is a cationic moietie that may be used in the construction of gene delivery vectors and DNA nanoparticles.

In vitro activity:

One compound in particular, [N-(cyclohexylmethyl)glycyl]-[N-(1-methylhexyl)glycyl]-[N-(4-methylbenzyl)glycyl]-[N-(2-(3-chlorophenyl)ethyl)glycyl]-lysyl-lysyl-lysine amide, showed high antibacterial activity and low toxicity toward red blood cells. Reference: Bioorg Med Chem. 2006 Jul 1;14(13):4444-51. https://pubmed.ncbi.nlm.nih.gov/16524733/

In vivo activity:

TBD

Preparing Stock Solutions

The following data is based on the product molecular weight 402.54 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.

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:

1. Ryge TS, Hansen PR. Potent antibacterial lysine-peptoid hybrids identified from a positional scanning combinatorial library. Bioorg Med Chem. 2006 Jul 1;14(13):4444-51. doi: 10.1016/j.bmc.2006.02.034. Epub 2006 Mar 9. PMID: 16524733.

In vitro protocol:

In vivo protocol:

TBD

1: Risteli M, Ruotsalainen H, Bergmann U, Venkatraman Girija U, Wallis R, Myllylä R. Lysyl hydroxylase 3 modifies lysine residues to facilitate oligomerization of mannan-binding lectin. PLoS One. 2014 Nov 24;9(11):e113498. doi: 10.1371/journal.pone.0113498. eCollection 2014. PubMed PMID: 25419660; PubMed Central PMCID: PMC4242627. 2: Bonnefond L, Castro de Moura M, Ribas de Pouplana L, Nureki O. Crystal structures of Entamoeba histolytica lysyl-tRNA synthetase reveal conformational changes upon lysine binding and a specific helix bundle domain. FEBS Lett. 2014 Nov 28;588(23):4478-86. PubMed PMID: 25448989. 3: Herranz N, Dave N, Millanes-Romero A, Morey L, Díaz VM, Lórenz-Fonfría V, Gutierrez-Gallego R, Jerónimo C, Di Croce L, García de Herreros A, Peiró S. Lysyl oxidase-like 2 deaminates lysine 4 in histone H3. Mol Cell. 2012 May 11;46(3):369-76. doi: 10.1016/j.molcel.2012.03.002. Epub 2012 Apr 5. Retraction in: Mol Cell. 2016 Jul 7;63(1):180. PubMed PMID: 22483618. 4: Gilreath MS, Roy H, Bullwinkle TJ, Katz A, Navarre WW, Ibba M. β-Lysine discrimination by lysyl-tRNA synthetase. FEBS Lett. 2011 Oct 20;585(20):3284-8. doi: 10.1016/j.febslet.2011.09.008. Epub 2011 Sep 12. PubMed PMID: 21925499; PubMed Central PMCID: PMC3196068. 5: Unoki M, Masuda A, Dohmae N, Arita K, Yoshimatsu M, Iwai Y, Fukui Y, Ueda K, Hamamoto R, Shirakawa M, Sasaki H, Nakamura Y. Lysyl 5-hydroxylation, a novel histone modification, by Jumonji domain containing 6 (JMJD6). J Biol Chem. 2013 Mar 1;288(9):6053-62. doi: 10.1074/jbc.M112.433284. Epub 2013 Jan 9. PubMed PMID: 23303181; PubMed Central PMCID: PMC3585044. 6: Herranz N, Dave N, Millanes-Romero A, Pascual-Reguant L, Morey L, Díaz VM, Lórenz-Fonfría V, Gutierrez-Gallego R, Jerónimo C, Iturbide A, Di Croce L, García de Herreros A, Peiró S. Lysyl oxidase-like 2 (LOXL2) oxidizes trimethylated lysine 4 in histone H3. FEBS J. 2016 Dec;283(23):4263-4273. doi: 10.1111/febs.13922. Epub 2016 Oct 30. PubMed PMID: 27735137. 7: Simon ES, Papoulias PG, Andrews PC. Selective collision-induced fragmentation of ortho-hydroxybenzyl-aminated lysyl-containing tryptic peptides. Rapid Commun Mass Spectrom. 2013 Jul 30;27(14):1619-30. doi: 10.1002/rcm.6611. PubMed PMID: 23765610. 8: Pestov NB, Okkelman IA, Shmanai VV, Hurski AL, Giaccia AJ, Shchepinov MS. Control of lysyl oxidase activity through site-specific deuteration of lysine. Bioorg Med Chem Lett. 2011 Jan 1;21(1):255-8. doi: 10.1016/j.bmcl.2010.11.018. Epub 2010 Nov 5. PubMed PMID: 21106372. 9: Ruotsalainen H, Risteli M, Wang C, Wang Y, Karppinen M, Bergmann U, Kvist AP, Pospiech H, Herzig KH, Myllylä R. The activities of lysyl hydroxylase 3 (LH3) regulate the amount and oligomerization status of adiponectin. PLoS One. 2012;7(11):e50045. doi: 10.1371/journal.pone.0050045. Epub 2012 Nov 29. PubMed PMID: 23209641; PubMed Central PMCID: PMC3510199. 10: Ambrogelly A, O'Donoghue P, Söll D, Moses S. A bacterial ortholog of class II lysyl-tRNA synthetase activates lysine. FEBS Lett. 2010 Jul 16;584(14):3055-60. doi: 10.1016/j.febslet.2010.05.036. Epub 2010 May 24. PubMed PMID: 20580719; PubMed Central PMCID: PMC2900529. 11: Asztalos P, Müller A, Hölke W, Sobek H, Rudolph MG. Atomic resolution structure of a lysine-specific endoproteinase from Lysobacter enzymogenes suggests a hydroxyl group bound to the oxyanion hole. Acta Crystallogr D Biol Crystallogr. 2014 Jul;70(Pt 7):1832-43. doi: 10.1107/S1399004714008463. Epub 2014 Jun 29. PubMed PMID: 25004961. 12: Yanagisawa T, Sumida T, Ishii R, Takemoto C, Yokoyama S. A paralog of lysyl-tRNA synthetase aminoacylates a conserved lysine residue in translation elongation factor P. Nat Struct Mol Biol. 2010 Sep;17(9):1136-43. doi: 10.1038/nsmb.1889. Epub 2010 Aug 22. PubMed PMID: 20729861. 13: Ryhänen L. Hydroxylation of lysyl residues in lysine-rich and arginine-rich histones by lysyl hydroxylase in vitro. Biochim Biophys Acta. 1975 Jul 27;397(1):50-7. PubMed PMID: 1148262. 14: Umehara T, Kim J, Lee S, Guo LT, Söll D, Park HS. N-acetyl lysyl-tRNA synthetases evolved by a CcdB-based selection possess N-acetyl lysine specificity in vitro and in vivo. FEBS Lett. 2012 Mar 23;586(6):729-33. doi: 10.1016/j.febslet.2012.01.029. Epub 2012 Jan 28. PubMed PMID: 22289181. 15: Chi H, Islam MS, Nsiama TK, Kato T, Nishino N. A convenient preparation of N (ε)-methyl-L-lysine derivatives and its application to the synthesis of histone tail peptides. Amino Acids. 2014 May;46(5):1305-11. doi: 10.1007/s00726-014-1690-6. Epub 2014 Feb 23. PubMed PMID: 24562477. 16: Kamalov M, Harris PW, Cooper GJ, Brimble MA. Site-specific cross-linking of collagen peptides by lysyl advanced glycation endproducts. Chem Commun (Camb). 2014 May 18;50(38):4944-6. doi: 10.1039/c4cc02003k. PubMed PMID: 24705519. 17: Shirota FN, Nagasawa HT, Elberling JA. Potential inhibitors of collagen biosynthesis. 5,5-Difluoro-DL-lysine and 5,5-dimethyl-DL-lysine and their activation by lysyl-tRNA ligase. J Med Chem. 1977 Dec;20(12):1623-7. PubMed PMID: 412965. 18: Liu Q, Chen X, Zeng X, Han D, Mao Z. [Purification, characterization and application of ε-poly-L. lysine- degrading enzyme from Streptomyces sp. M-Z18 ]. Wei Sheng Wu Xue Bao. 2014 Sep 4;54(9):1022-32. Chinese. PubMed PMID: 25522591. 19: Xu L, Go EP, Finney J, Moon H, Lantz M, Rebecchi K, Desaire H, Mure M. Post-translational modifications of recombinant human lysyl oxidase-like 2 (rhLOXL2) secreted from Drosophila S2 cells. J Biol Chem. 2013 Feb 22;288(8):5357-63. doi: 10.1074/jbc.C112.421768. Epub 2013 Jan 14. PubMed PMID: 23319596; PubMed Central PMCID: PMC3581389. 20: Roy H, Zou SB, Bullwinkle TJ, Wolfe BS, Gilreath MS, Forsyth CJ, Navarre WW, Ibba M. The tRNA synthetase paralog PoxA modifies elongation factor-P with (R)-β-lysine. Nat Chem Biol. 2011 Aug 14;7(10):667-9. doi: 10.1038/nchembio.632. PubMed PMID: 21841797; PubMed Central PMCID: PMC3177975.