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MedKoo Cat#: 597522 | Name: Lipoyllysine

Description:

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

Lipoyllysine is a substrate of lipoamidase.

Chemical Structure

Lipoyllysine
CAS#20902-53-8

Theoretical Analysis

MedKoo Cat#: 597522

Name: Lipoyllysine

CAS#: 20902-53-8

Chemical Formula: C14H28N2O4S2

Exact Mass:

Molecular Weight: 352.50

Elemental Analysis: C, 47.70; H, 8.01; N, 7.95; O, 18.15; S, 18.19

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
Lipoyllysine; DL-Lipoyl-L-lysine;
IUPAC/Chemical Name
L-lysine compound with 5-(1,2-dithiolan-3-yl)pentanoic acid (1:1)
InChi Key
WCHWQPTUXDMALZ-ZSCHJXSPSA-N
InChi Code
InChI=1S/C8H14O2S2.C6H14N2O2/c9-8(10)4-2-1-3-7-5-6-11-12-7;7-4-2-1-3-5(8)6(9)10/h7H,1-6H2,(H,9,10);5H,1-4,7-8H2,(H,9,10)/t;5-/m.0/s1
SMILES Code
N[C@@H](CCCCN)C(O)=O.O=C(O)CCCCC1SSCC1
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 352.50 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
1: Motafakkerazad R, Wang MY, Wada N, Matsugo S, Konishi T. Simple HPLC evaluation of lipoamidase activity in tissue using a newly synthesized fluorescent substrate, dansyl-α-lipoyllysine. J Nutr Sci Vitaminol (Tokyo). 2011;57(5):377-82. Erratum in: J Nutr Sci Vitaminol (Tokyo). 2012;58(1):68. PubMed PMID: 22293216. 2: Khanna S, Atalay M, Lodge JK, Laaksonen DE, Roy S, Hanninen O, Packer L, Sen CK. Skeletal muscle and liver lipoyllysine content in response to exercise, training and dietary alpha-lipoic acid supplementation. Biochem Mol Biol Int. 1998 Oct;46(2):297-306. PubMed PMID: 9801798. 3: Satoh S, Shindoh M, Min JZ, Toyo'oka T, Fukushima T, Inagaki S. Selective and sensitive determination of lipoyllysine (protein-bound alpha-lipoic acid) in biological specimens by high-performance liquid chromatography with fluorescence detection. Anal Chim Acta. 2008 Jun 23;618(2):210-7. doi: 10.1016/j.aca.2008.05.001. Epub 2008 May 7. PubMed PMID: 18513542. 4: Fujiwara K, Okamura-Ikeda K, Motokawa Y. Lipoylation of H-protein of the glycine cleavage system. The effect of site-directed mutagenesis of amino acid residues around the lipoyllysine residue on the lipoate attachment. FEBS Lett. 1991 Nov 18;293(1-2):115-8. PubMed PMID: 1959641. 5: Hayakawa K, Oizumi J. Determination of lipoyllysine derived from enzymes by liquid chromatography. J Chromatogr. 1989 May 5;490(1):33-41. PubMed PMID: 2503531. 6: Akiba S, Matsugo S, Packer L, Konishi T. Assay of protein-bound lipoic acid in tissues by a new enzymatic method. Anal Biochem. 1998 May 1;258(2):299-304. PubMed PMID: 9570844. 7: Backman-Gullers B, Hannestad U, Nilsson L, Sörbo B. Studies on lipoamidase: characterization of the enzyme in human serum and breast milk. Clin Chim Acta. 1990 Oct 31;191(1-2):49-60. PubMed PMID: 2127386. 8: Nilsson L, Kågedal B. Lipoamidase and biotinidase activities in the rat: tissue distribution and intracellular localization. Eur J Clin Chem Clin Biochem. 1994 Jul;32(7):501-9. PubMed PMID: 7981329. 9: Fujiwara K, Okamura-Ikeda K, Motokawa Y. Chicken liver H-protein, a component of the glycine cleavage system. Amino acid sequence and identification of the N epsilon-lipoyllysine residue. J Biol Chem. 1986 Jul 5;261(19):8836-41. PubMed PMID: 3522581. 10: Mattulat A, Baltes W. Determination of lipoic acid in meat of commercial quality. Z Lebensm Unters Forsch. 1992 Apr;194(4):326-9. PubMed PMID: 1598790. 11: Allina J, Hu B, Sullivan DM, Fiel MI, Thung SN, Bronk SF, Huebert RC, van de Water J, LaRusso NF, Gershwin ME, Gores GJ, Odin JA. T cell targeting and phagocytosis of apoptotic biliary epithelial cells in primary biliary cirrhosis. J Autoimmun. 2006 Dec;27(4):232-41. Epub 2007 Jan 10. PubMed PMID: 17222534. 12: Oizumi J, Hayakawa K. Release of anchored membrane enzymes by lipoamidase. Mol Cell Biochem. 1992 Sep 22;115(1):11-7. PubMed PMID: 1435760. 13: Nilsson L, Ronge E. Lipoamidase and biotinidase deficiency: evidence that lipoamidase and biotinidase are the same enzyme in human serum. Eur J Clin Chem Clin Biochem. 1992 Mar;30(3):119-26. PubMed PMID: 1599976. 14: Raddatz G, Bisswanger H. Receptor site and stereospecifity of dihydrolipoamide dehydrogenase for R- and S-lipoamide: a molecular modeling study. J Biotechnol. 1997 Oct 17;58(2):89-100. PubMed PMID: 9383983. 15: Rentier C, Pacini G, Nuti F, Peroni E, Rovero P, Papini AM. Synthesis of diastereomerically pure Lys(Nε-lipoyl) building blocks and their use in Fmoc/tBu solid phase synthesis of lipoyl-containing peptides for diagnosis of primary biliary cirrhosis. J Pept Sci. 2015 May;21(5):408-14. doi: 10.1002/psc.2761. Epub 2015 Mar 26. PubMed PMID: 25820084. 16: Oizumi J, Hayakawa K. Liberation of lipoate by human serum lipoamidase from bovine heart pyruvate dehydrogenase. Biochem Biophys Res Commun. 1989 Jul 31;162(2):658-63. PubMed PMID: 2502979. 17: Packer L, Cadenas E. Lipoic acid: energy metabolism and redox regulation of transcription and cell signaling. J Clin Biochem Nutr. 2011 Jan;48(1):26-32. doi: 10.3164/jcbn.11-005FR. Epub 2010 Dec 29. PubMed PMID: 21297908; PubMed Central PMCID: PMC3022059. 18: Bradford AP, Aitken A, Beg F, Cook KG, Yeaman SJ. Amino acid sequence surrounding the lipoic acid cofactor of bovine kidney 2-oxoglutarate dehydrogenase complex. FEBS Lett. 1987 Sep 28;222(1):211-4. PubMed PMID: 3115829. 19: Ghibu S, Richard C, Vergely C, Zeller M, Cottin Y, Rochette L. Antioxidant properties of an endogenous thiol: Alpha-lipoic acid, useful in the prevention of cardiovascular diseases. J Cardiovasc Pharmacol. 2009 Nov;54(5):391-8. Review. PubMed PMID: 19998523. 20: Konishi T, Handelman G, Matsugo S, Mathur VV, Tritschler HJ, Packer L. Amplified determination of lipoyl groups by lipoamide dehydrogenase in the presence of oxidized glutathione. Biochem Mol Biol Int. 1996 May;38(6):1155-61. PubMed PMID: 8739037.