Tetralysine | CAS#997-20-6 | cationic moietie

MedKoo Cat#: 597538 | Name: Tetralysine

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Description:

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

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

Chemical Structure

Tetralysine

CAS#997-20-6

Theoretical Analysis

MedKoo Cat#: 597538

Name: Tetralysine

CAS#: 997-20-6

Chemical Formula: C24H50N8O5

Exact Mass: 530.3904

Molecular Weight: 530.71

Elemental Analysis: C, 54.32; H, 9.50; N, 21.11; O, 15.07

Price and Availability

Size	Price	Availability	Quantity
10mg	USD 300.00
50mg	USD 660.00

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Synonym

Tetralysine;

IUPAC/Chemical Name

L-lysyl-L-lysyl-L-lysyl-L-lysine

InChi Key

RRBGTUQJDFBWNN-MUGJNUQGSA-N

InChi Code

InChI=1S/C24H50N8O5/c25-13-5-1-9-17(29)21(33)30-18(10-2-6-14-26)22(34)31-19(11-3-7-15-27)23(35)32-20(24(36)37)12-4-8-16-28/h17-20H,1-16,25-29H2,(H,30,33)(H,31,34)(H,32,35)(H,36,37)/t17-,18-,19-,20-/m0/s1

SMILES Code

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 530.71 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

1: Zhang C, Zhao Z, Jia YJ, Zhang PQ, Sun Y, Zhou YC, Wang GX, Zhu B. Rationally Designed Self-Assembling Nanovaccines Elicit Robust Mucosal and Systemic Immunity against Rhabdovirus. ACS Appl Mater Interfaces. 2024 Jan 10;16(1):228-244. doi: 10.1021/acsami.3c14305. Epub 2023 Dec 6. PMID: 38055273. 2: Kaur A, Piplani S, Kaushik D, Fung J, Sakala IG, Honda-Okubo Y, Mehta SK, Petrovsky N, Salunke DB. Stereoisomeric Pam2CS based TLR2 agonists: synthesis, structural modelling and activity as vaccine adjuvants. RSC Med Chem. 2022 Apr 20;13(5):622-637. doi: 10.1039/d1md00372k. PMID: 35694694; PMCID: PMC9132229. 3: Dirksmeyer T, Stahl P, Vallet C, Knauer S, Giese M, Schmuck C, Hirschhäuser C. Advances towards Cell-Specific Gene Transfection: A Small-Molecule Approach Allows Order-of-Magnitude Selectivity. Chemistry. 2022 Aug 1;28(43):e202104618. doi: 10.1002/chem.202104618. Epub 2022 Jun 17. PMID: 35604769; PMCID: PMC9401007. 4: Pan X, Pei X, Huang H, Su N, Wu Z, Wu Z, Qi X. One-in-one individual package and delivery of CRISPR/Cas9 ribonucleoprotein using apoferritin. J Control Release. 2021 Sep 10;337:686-697. doi: 10.1016/j.jconrel.2021.08.015. Epub 2021 Aug 10. PMID: 34389365. 5: Read C, Schauflinger M, Nikolaenko D, Walther P, von Einem J. Regulation of Human Cytomegalovirus Secondary Envelopment by a C-Terminal Tetralysine Motif in pUL71. J Virol. 2019 Jun 14;93(13):e02244-18. doi: 10.1128/JVI.02244-18. PMID: 30996102; PMCID: PMC6580969. 6: Kaur A, Poonam, Patil MT, Mehta SK, Salunke DB. An efficient and scalable synthesis of potent TLR2 agonistic PAM2CSK4. RSC Adv. 2018 Mar 5;8(18):9587-9596. doi: 10.1039/c8ra01387j. PMID: 35540846; PMCID: PMC9078680. 7: Davenport KR, Smith CA, Hofstetter H, Horn JR, Hofstetter O. Site-directed immobilization of a genetically engineered anti-methotrexate antibody via an enzymatically introduced biotin label significantly increases the binding capacity of immunoaffinity columns. J Chromatogr B Analyt Technol Biomed Life Sci. 2016 May 15;1021:114-121. doi: 10.1016/j.jchromb.2016.01.021. Epub 2016 Jan 15. PMID: 26809205. 8: Ghobadi AF, Letteri R, Parelkar SS, Zhao Y, Chan-Seng D, Emrick T, Jayaraman A. Dispersing Zwitterions into Comb Polymers for Nonviral Transfection: Experiments and Molecular Simulation. Biomacromolecules. 2016 Feb 8;17(2):546-57. doi: 10.1021/acs.biomac.5b01462. Epub 2016 Jan 7. PMID: 26741292. 9: Li M, Schlesiger S, Knauer SK, Schmuck C. A tailor-made specific anion- binding motif in the side chain transforms a tetrapeptide into an efficient vector for gene delivery. Angew Chem Int Ed Engl. 2015 Mar 2;54(10):2941-4. doi: 10.1002/anie.201410429. Epub 2015 Jan 22. PMID: 25614369. 10: Coussot G, Ladner Y, Bayart C, Faye C, Vigier V, Perrin C. On-line capillary electrophoresis-based enzymatic methodology for the study of polymer-drug conjugates. J Chromatogr A. 2015 Jan 9;1376:159-66. doi: 10.1016/j.chroma.2014.12.029. Epub 2014 Dec 12. PMID: 25537173. 11: Ke MR, Eastel JM, Ngai KL, Cheung YY, Chan PK, Hui M, Ng DK, Lo PC. Oligolysine-conjugated zinc(II) phthalocyanines as efficient photosensitizers for antimicrobial photodynamic therapy. Chem Asian J. 2014 Jul;9(7):1868-75. doi: 10.1002/asia.201402025. Epub 2014 May 5. PMID: 24799418. 12: Guan JY, Foerster JM, Drijfhout JW, Timmer M, Blok A, Ullmann GM, Ubbink M. An ensemble of rapidly interconverting orientations in electrostatic protein- peptide complexes characterized by NMR spectroscopy. Chembiochem. 2014 Mar 3;15(4):556-66. doi: 10.1002/cbic.201300623. Epub 2014 Feb 6. PMID: 24504673. 13: Minsky BB, Nguyen TV, Peyton SR, Kaltashov IA, Dubin PL. Heparin decamer bridges a growth factor and an oligolysine by different charge-driven interactions. Biomacromolecules. 2013 Nov 11;14(11):4091-8. doi: 10.1021/bm401227p. Epub 2013 Oct 31. PMID: 24107074. 14: Urakami H, Hentschel J, Seetho K, Zeng H, Chawla K, Guan Z. Surfactant-free synthesis of biodegradable, biocompatible, and stimuli-responsive cationic nanogel particles. Biomacromolecules. 2013 Oct 14;14(10):3682-8. doi: 10.1021/bm401039r. Epub 2013 Sep 30. PMID: 24047127. 15: Kassa R, Monterroso V, David LL, Tshala-Katumbay D. Diagnostic and therapeutic potential of tetanus toxin-derivatives in neurological diseases. J Mol Neurosci. 2013 Nov;51(3):788-91. doi: 10.1007/s12031-013-0065-x. Epub 2013 Jul 11. PMID: 23842888; PMCID: PMC3838929. 16: Muse O, Zengeya T, Mwaura J, Hnedzko D, McGee DW, Grewer CT, Rozners E. Sequence selective recognition of double-stranded RNA at physiologically relevant conditions using PNA-peptide conjugates. ACS Chem Biol. 2013 Aug 16;8(8):1683-6. doi: 10.1021/cb400144x. Epub 2013 Jun 12. PMID: 23721369; PMCID: PMC3745792. 17: Wernersson E, Heyda J, Kubíčková A, Křížek T, Coufal P, Jungwirth P. Counterion condensation in short cationic peptides: limiting mobilities beyond the Onsager-Fuoss theory. Electrophoresis. 2012 Mar;33(6):981-9. doi: 10.1002/elps.201100602. PMID: 22528417. 18: Breloy I, Pacharra S, Ottis P, Bonar D, Grahn A, Hanisch FG. O-linked N,N'-diacetyllactosamine (LacdiNAc)-modified glycans in extracellular matrix glycoproteins are specifically phosphorylated at subterminal N-acetylglucosamine. J Biol Chem. 2012 May 25;287(22):18275-86. doi: 10.1074/jbc.M111.280297. Epub 2012 Apr 3. PMID: 22474328; PMCID: PMC3365741. 19: Wernersson E, Heyda J, Kubícková A, Krízek T, Coufal P, Jungwirth P. Effect of association with sulfate on the electrophoretic mobility of polyarginine and polylysine. J Phys Chem B. 2010 Sep 16;114(36):11934-41. doi: 10.1021/jp1054342. PMID: 20726540. 20: Soenen SJ, Illyes E, Vercauteren D, Braeckmans K, Majer Z, De Smedt SC, De Cuyper M. The role of nanoparticle concentration-dependent induction of cellular stress in the internalization of non-toxic cationic magnetoliposomes. Biomaterials. 2009 Dec;30(36):6803-13. doi: 10.1016/j.biomaterials.2009.08.050. Epub 2009 Sep 17. PMID: 19765821.