MedKoo Cat#: 597489 | Name: Lysyllysine

Description:

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

Lysyllysine is a dipeptide composed of two lysine residues. It is an incomplete breakdown product of protein digestion or protein catabolism. Some dipeptides are known to have physiological or cell-signaling effects although most are simply short-lived intermediates on their way to specific amino acid degradation pathways following further proteolysis. This dipeptide has not yet been identified in human tissues or biofluids and so it is classified as an 'Expected' metabolite.

Chemical Structure

Lysyllysine
Lysyllysine
CAS#13184-13-9

Theoretical Analysis

MedKoo Cat#: 597489

Name: Lysyllysine

CAS#: 13184-13-9

Chemical Formula: C12H26N4O3

Exact Mass: 274.2005

Molecular Weight: 274.36

Elemental Analysis: C, 52.53; H, 9.55; N, 20.42; O, 17.49

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
Lysyllysine; Lys-lys; L-Lys-L-lys;
IUPAC/Chemical Name
L-lysyl-L-lysine
InChi Key
NVGBPTNZLWRQSY-UWVGGRQHSA-N
InChi Code
InChI=1S/C12H26N4O3/c13-7-3-1-5-9(15)11(17)16-10(12(18)19)6-2-4-8-14/h9-10H,1-8,13-15H2,(H,16,17)(H,18,19)/t9-,10-/m0/s1
SMILES Code
NCCCC[C@@H](C(O)=O)NC([C@H](CCCCN)N)=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 274.36 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
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PubMed PMID: 26941332; PubMed Central PMCID: PMC4831884. 5: Sleigh SH, Tame JR, Dodson EJ, Wilkinson AJ. Peptide binding in OppA, the crystal structures of the periplasmic oligopeptide binding protein in the unliganded form and in complex with lysyllysine. Biochemistry. 1997 Aug 12;36(32):9747-58. PubMed PMID: 9245406. 6: Ma Y, Liu J, Shi H, Yu LL. Isolation and characterization of anti-inflammatory peptides derived from whey protein. J Dairy Sci. 2016 Sep;99(9):6902-6912. doi: 10.3168/jds.2016-11186. Epub 2016 Jul 7. PubMed PMID: 27394940. 7: Toyokuni T, Hakomori S. Carbohydrate-lysyllysine conjugates as cell antiadhesion agents. Methods Enzymol. 1994;247:325-41. PubMed PMID: 7898361. 8: Kojima N, Fenderson BA, Stroud MR, Goldberg RI, Habermann R, Toyokuni T, Hakomori S. Further studies on cell adhesion based on Le(x)-Le(x) interaction, with new approaches: embryoglycan aggregation of F9 teratocarcinoma cells, and adhesion of various tumour cells based on Le(x) expression. Glycoconj J. 1994 Jun;11(3):238-48. PubMed PMID: 7841799. 9: Custer SK, Todd AG, Singh NN, Androphy EJ. Dilysine motifs in exon 2b of SMN protein mediate binding to the COPI vesicle protein α-COP and neurite outgrowth in a cell culture model of spinal muscular atrophy. Hum Mol Genet. 2013 Oct 15;22(20):4043-52. doi: 10.1093/hmg/ddt254. Epub 2013 May 31. PubMed PMID: 23727837; PubMed Central PMCID: PMC3988423. 10: Jackson LP, Lewis M, Kent HM, Edeling MA, Evans PR, Duden R, Owen DJ. Molecular basis for recognition of dilysine trafficking motifs by COPI. Dev Cell. 2012 Dec 11;23(6):1255-62. doi: 10.1016/j.devcel.2012.10.017. Epub 2012 Nov 21. PubMed PMID: 23177648; PubMed Central PMCID: PMC3521961. 11: Barouch WW. Carboxypeptidase P cleaves Lys-Lys. Pept Res. 1990 Mar-Apr;3(2):73-4. PubMed PMID: 2134052. 12: Yang WY, Roy S, Phrathep B, Rengert Z, Kenworthy R, Zorio DA, Alabugin IV. Engineering pH-gated transitions for selective and efficient double-strand DNA photocleavage in hypoxic tumors. J Med Chem. 2011 Dec 22;54(24):8501-16. doi: 10.1021/jm2010282. Epub 2011 Nov 22. PubMed PMID: 22050291. 13: Khachigian LM, Evin G, Morgan FJ, Owensby DA, Chesterman CN. A crossreactive antipeptide monoclonal antibody with specificity for lysyl-lysine. J Immunol Methods. 1991 Jul 5;140(2):249-58. Erratum in: J Immunol Methods 1992 May 18;149(2):267. PubMed PMID: 1712372. 14: Hasegawa H, Liu L, Nishimura M. Dilysine retrieval signal-containing p24 proteins collaborate in inhibiting γ-cleavage of amyloid precursor protein. J Neurochem. 2010 Nov;115(3):771-81. doi: 10.1111/j.1471-4159.2010.06977.x. Epub 2010 Sep 28. PubMed PMID: 20807314. 15: Cosson P, Schröder-Köhne S, Sweet DS, Démollière C, Hennecke S, Frigerio G, Letourneur F. The Sec20/Tip20p complex is involved in ER retrieval of dilysine-tagged proteins. Eur J Cell Biol. 1997 Jun;73(2):93-7. 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On the charge partitioning between c and z fragments formed after electron-capture induced dissociation of charge-tagged Lys-Lys and Ala-Lys dipeptide dications. J Am Soc Mass Spectrom. 2009 Oct;20(10):1881-9. doi: 10.1016/j.jasms.2009.06.015. Epub 2009 Jul 3. PubMed PMID: 19651526. 20: Letourneur F, Gaynor EC, Hennecke S, Démollière C, Duden R, Emr SD, Riezman H, Cosson P. Coatomer is essential for retrieval of dilysine-tagged proteins to the endoplasmic reticulum. Cell. 1994 Dec 30;79(7):1199-207. PubMed PMID: 8001155.