Cysteinyllysine | CAS#71190-90-4 | dipeptide

MedKoo Cat#: 597520 | Name: Cysteinyllysine

Description:

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

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

Cysteinyllysine

CAS#71190-90-4

Theoretical Analysis

MedKoo Cat#: 597520

Name: Cysteinyllysine

CAS#: 71190-90-4

Chemical Formula: C9H19N3O3S

Exact Mass: 249.1147

Molecular Weight: 249.32

Elemental Analysis: C, 43.36; H, 7.68; N, 16.85; O, 19.25; S, 12.86

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 #

No Data

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

Instruction

View handling instruction

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.

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: Miranti EH, Freedman ND, Weinstein SJ, Abnet CC, Selhub J, Murphy G, Diaw L, Männistö S, Taylor PR, Albanes D, Stolzenberg-Solomon RZ. Prospective study of serum cysteine and cysteinylglycine and cancer of the head and neck, esophagus, and stomach in a cohort of male smokers. Am J Clin Nutr. 2016 Sep;104(3):686-93. doi: 10.3945/ajcn.115.125799. Epub 2016 Aug 17. PubMed PMID: 27534643; PubMed Central PMCID: PMC4997291. 2: Zhang W, Li P, Geng Q, Duan Y, Guo M, Cao Y. Simultaneous determination of glutathione, cysteine, homocysteine, and cysteinylglycine in biological fluids by ion-pairing high-performance liquid chromatography coupled with precolumn derivatization. J Agric Food Chem. 2014 Jun 25;62(25):5845-52. doi: 10.1021/jf5014007. Epub 2014 Jun 17. PubMed PMID: 24914733. 3: Poon JC, Josephy PD. Hydrolysis of S-aryl-cysteinylglycine conjugates catalyzed by porcine kidney cortex membrane dipeptidase. Xenobiotica. 2012 Dec;42(12):1178-86. doi: 10.3109/00498254.2012.700427. Epub 2012 Jun 29. PubMed PMID: 22742779. 4: Ferreira-Lima N, Vallverdú-Queralt A, Meudec E, Mazauric JP, Sommerer N, Bordignon-Luiz MT, Cheynier V, Le Guernevé C. Synthesis, Identification, and Structure Elucidation of Adducts Formed by Reactions of Hydroxycinnamic Acids with Glutathione or Cysteinylglycine. J Nat Prod. 2016 Sep 23;79(9):2211-22. doi: 10.1021/acs.jnatprod.6b00279. Epub 2016 Sep 12. PubMed PMID: 27616743. 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. 8: Jösch C, Sies H, Akerboom TP. Hepatic mercapturic acid formation: involvement of cytosolic cysteinylglycine S-conjugate dipeptidase activity. Biochem Pharmacol. 1998 Sep 15;56(6):763-71. PubMed PMID: 9751082. 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.