Cysteinyllysine

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

MedKoo CAT#: 597520

CAS#: 71190-90-4

Description: Cysteinyllysine is a dipeptide composed of cysteine and lysine. 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.

Chemical Structure

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Cysteinyllysine
CAS# 71190-90-4
Instruction

Theoretical Analysis

MedKoo Cat#: 597520
Name: Cysteinyllysine
CAS#: 71190-90-4
Chemical Formula: C9H19N3O3S
Exact Mass: 249.11
Molecular Weight: 249.320
Elemental Analysis: C, 43.36; H, 7.68; N, 16.85; O, 19.25; S, 12.86

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

Synonym: Cysteinyllysine; L-Lysine, N2-L-cysteinyl-; L-Lysine, L-cysteinyl-;

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

InChi Key: WXOFKRKAHJQKLT-BQBZGAKWSA-N

InChi Code: InChI=1S/C9H19N3O3S/c10-4-2-1-3-7(9(14)15)12-8(13)6(11)5-16/h6-7,16H,1-5,10-11H2,(H,12,13)(H,14,15)/t6-,7-/m0/s1

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

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 249.32 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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5: Steele ML, Fuller S, Patel M, Kersaitis C, Ooi L, Münch G. Effect of Nrf2 activators on release of glutathione, cysteinylglycine and homocysteine by human U373 astroglial cells. Redox Biol. 2013 Sep 12;1:441-5. doi: 10.1016/j.redox.2013.08.006. eCollection 2013. PubMed PMID: 24191238; PubMed Central PMCID: PMC3814960.

6: Morris J, Leslie SW. Glutamate and cysteinylglycine effects on NMDA receptors: inhibition by ethanol. Alcohol. 1996 Mar-Apr;13(2):157-62. PubMed PMID: 8814650.

7: Aug A, Altraja A, Altraja S, Laaniste L, Mahlapuu R, Soomets U, Kilk K. Alterations of bronchial epithelial metabolome by cigarette smoke are reversible by an antioxidant, O-methyl-L-tyrosinyl-γ-L-glutamyl-L-cysteinylglycine. Am J Respir Cell Mol Biol. 2014 Oct;51(4):586-94. doi: 10.1165/rcmb.2013-0377OC. PubMed PMID: 24810251.

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9: Pinna A, Zinellu A, Franconi F, Solinas G, Carru C. Decreased plasma cysteinylglycine and taurine levels in branch retinal vein occlusion. Ophthalmic Res. 2010;43(1):26-32. doi: 10.1159/000246575. Epub 2009 Oct 14. PubMed PMID: 19829009.

10: Carlsson J, Larsen JT, Edlund MB. Utilization of glutathione (L-gamma-glutamyl-L-cysteinylglycine) by Fusobacterium nucleatum subspecies nucleatum. Oral Microbiol Immunol. 1994 Oct;9(5):297-300. PubMed PMID: 7808772.

11: Lin J, Manson JE, Selhub J, Buring JE, Zhang SM. Plasma cysteinylglycine levels and breast cancer risk in women. Cancer Res. 2007 Dec 1;67(23):11123-7. PubMed PMID: 18056435.

12: Jösch C, Klotz LO, Sies H. Identification of cytosolic leucyl aminopeptidase (EC 3.4.11.1) as the major cysteinylglycine-hydrolysing activity in rat liver. Biol Chem. 2003 Feb;384(2):213-8. PubMed PMID: 12675513.

13: Anni H, Pristatsky P, Israel Y. Binding of acetaldehyde to a glutathione metabolite: mass spectrometric characterization of an acetaldehyde-cysteinylglycine conjugate. Alcohol Clin Exp Res. 2003 Oct;27(10):1613-21. PubMed PMID: 14574232.

14: Badiou S, Bellet H, Lehmann S, Cristol JP, Jaber S. Elevated plasma cysteinylglycine levels caused by cilastatin-associated antibiotic treatment. Clin Chem Lab Med. 2005;43(3):332-4. PubMed PMID: 15843241.

15: Ferin R, Pavão ML, Baptista J. Methodology for a rapid and simultaneous determination of total cysteine, homocysteine, cysteinylglycine and glutathione in plasma by isocratic RP-HPLC. J Chromatogr B Analyt Technol Biomed Life Sci. 2012 Dec 12;911:15-20. doi: 10.1016/j.jchromb.2012.10.022. Epub 2012 Oct 24. PubMed PMID: 23217300.

16: Sergueeva AI, Miasnikova GY, Okhotin DJ, Levina AA, Debebe Z, Ammosova T, Niu X, Romanova EA, Nekhai S, DiBello PM, Jacobsen DW, Prchal JT, Gordeuk VR. Elevated homocysteine, glutathione and cysteinylglycine concentrations in patients homozygous for the Chuvash polycythemia VHL mutation. Haematologica. 2008 Feb;93(2):279-82. doi: 10.3324/haematol.11851. Epub 2008 Jan 26. PubMed PMID: 18223282; PubMed Central PMCID: PMC2852873.

17: Mansoor MA, Svardal AM, Ueland PM. Determination of the in vivo redox status of cysteine, cysteinylglycine, homocysteine, and glutathione in human plasma. Anal Biochem. 1992 Feb 1;200(2):218-29. PubMed PMID: 1632485.

18: Zinellu A, Pinna A, Zinellu E, Sotgia S, Deiana L, Carru C. High-throughput capillary electrophoresis method for plasma cysteinylglycine measurement: evidences for a clinical application. Amino Acids. 2008 Jan;34(1):69-74. Epub 2007 Aug 17. PubMed PMID: 17704893.

19: Pastore A, Massoud R, Motti C, Lo Russo A, Fucci G, Cortese C, Federici G. Fully automated assay for total homocysteine, cysteine, cysteinylglycine, glutathione, cysteamine, and 2-mercaptopropionylglycine in plasma and urine. Clin Chem. 1998 Apr;44(4):825-32. PubMed PMID: 9554495.

20: Kera Y, Kiriyama T, Komura S. Conjugation of acetaldehyde with cysteinylglycine, the first metabolite in glutathione breakdown by gamma-glutamyltranspeptidase. Agents Actions. 1985 Oct;17(1):48-52. PubMed PMID: 2867670.