Lysinoalanine | CAS#18810-04-3 | amino acid

MedKoo Cat#: 597527 | Name: Lysinoalanine

Description:

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

Lysinoalanine is an unusual amino acid, not a dipeptide, which has been found in proteins of cooked foods. It is formed in food that is heated or treated with alkali. Has been implicated in nephrocytomegalia in rats.

Chemical Structure

Lysinoalanine

CAS#18810-04-3

Theoretical Analysis

MedKoo Cat#: 597527

Name: Lysinoalanine

CAS#: 18810-04-3

Chemical Formula: C9H19N3O4

Exact Mass: 233.1376

Molecular Weight: 233.26

Elemental Analysis: C, 46.34; H, 8.21; N, 18.01; O, 27.43

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

Lysinoalanine; LAL; CCRIS 5632; CCRIS-5632; CCRIS5632;

IUPAC/Chemical Name

N6-(2-amino-2-carboxyethyl)-L-lysine

InChi Key

IMSOBGJSYSFTKG-PKPIPKONSA-N

InChi Code

InChI=1S/C9H19N3O4/c10-6(8(13)14)3-1-2-4-12-5-7(11)9(15)16/h6-7,12H,1-5,10-11H2,(H,13,14)(H,15,16)/t6-,7?/m0/s1

SMILES Code

N[C@@H](CCCCNCC(N)C(O)=O)C(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 233.26 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: Luo XY, Tu YG, Zhao Y, Li JK, Wang JJ. Effects of sulfhydryl compounds, carbohydrates, organic acids, and sodium sulfite on the formation of lysinoalanine in preserved egg. J Food Sci. 2014 Aug;79(8):T1621-8. doi: 10.1111/1750-3841.12543. Epub 2014 Jul 21. PubMed PMID: 25047093. 2: Hellwig M, Matthes R, Peto A, Löbner J, Henle T. N-ε-fructosyllysine and N-ε-carboxymethyllysine, but not lysinoalanine, are available for absorption after simulated gastrointestinal digestion. Amino Acids. 2014 Feb;46(2):289-99. doi: 10.1007/s00726-013-1501-5. Epub 2013 Apr 23. PubMed PMID: 23609106. 3: Zhao Y, Luo X, Li J, Xu M, Tu Y. Effect of basic alkali-pickling conditions on the production of lysinoalanine in preserved eggs. Poult Sci. 2015 Sep;94(9):2272-9. doi: 10.3382/ps/pev184. Epub 2015 Jul 17. PubMed PMID: 26188034. 4: Zhao Y, Luo X, Li J, Xu M, Tu Y. Formation of lysinoalanine in egg white under alkali treatment. Poult Sci. 2016 Mar;95(3):660-7. doi: 10.3382/ps/pev372. Epub 2016 Jan 15. PubMed PMID: 26772660. 5: Rombouts I, Lambrecht MA, Carpentier SC, Delcour JA. Identification of lanthionine and lysinoalanine in heat-treated wheat gliadin and bovine serum albumin using tandem mass spectrometry with higher-energy collisional dissociation. Amino Acids. 2016 Apr;48(4):959-71. doi: 10.1007/s00726-015-2139-2. Epub 2015 Dec 11. PubMed PMID: 26661033. 6: Miller MR, Miller KA, Bian J, James ME, Zhang S, Lynch MJ, Callery PS, Hettick JM, Cockburn A, Liu J, Li C, Crane BR, Charon NW. Spirochaete flagella hook proteins self-catalyse a lysinoalanine covalent crosslink for motility. Nat Microbiol. 2016 Aug 8;1(10):16134. doi: 10.1038/nmicrobiol.2016.134. PubMed PMID: 27670115; PubMed Central PMCID: PMC5077173. 7: Friedman M. Inhibition of lysinoalanine synthesis by protein acylation. Adv Exp Med Biol. 1978;105:613-48. PubMed PMID: 569426. 8: Corpet DE, Taché S, Archer MC, Bruce WR. Dehydroalanine and lysinoalanine in thermolyzed casein do not promote colon cancer in the rat. Food Chem Toxicol. 2008 Sep;46(9):3037-42. doi: 10.1016/j.fct.2008.06.002. Epub 2008 Jun 10. PubMed PMID: 18585427. 9: Hayashi R. Lysinoalanine as a metal chelator. An implication for toxicity. J Biol Chem. 1982 Dec 10;257(23):13896-8. PubMed PMID: 6815182. 10: Pfaender P. Lysinoalanine--a toxic compound in processed proteinaceous foods. World Rev Nutr Diet. 1983;41:97-109. Review. PubMed PMID: 6428067. 11: Friedman M, Grosjean OK, Zahnley JC. Inactivation of metalloenzymes by lysinoalanine, phenylethylaminoalanine, alkali-treated food proteins, and sulfur amino acids. Adv Exp Med Biol. 1986;199:531-60. PubMed PMID: 3026144. 12: Fritsch RJ, Hoffmann H, Klostermeyer H. Formation of lysinoalanine during heat treatment of milk. Z Lebensm Unters Forsch. 1983;176(5):341-5. PubMed PMID: 6412474. 13: Friedman M. Lysinoalanine in food and in antimicrobial proteins. Adv Exp Med Biol. 1999;459:145-59. Review. PubMed PMID: 10335374. 14: Somoza V, Wenzel E, Weiss C, Clawin-Rädecker I, Grübel N, Erbersdobler HF. Dose-dependent utilisation of casein-linked lysinoalanine, N(epsilon)-fructoselysine and N(epsilon)-carboxymethyllysine in rats. Mol Nutr Food Res. 2006 Sep;50(9):833-41. PubMed PMID: 16917812. 15: Lifsey BJ Jr, Farkas WR, Reyniers JP. Interaction of lysinoalanine with the protein synthesizing apparatus. Chem Biol Interact. 1988;68(3-4):241-57. PubMed PMID: 3145818. 16: Friedman M. Chemistry, biochemistry, nutrition, and microbiology of lysinoalanine, lanthionine, and histidinoalanine in food and other proteins. J Agric Food Chem. 1999 Apr;47(4):1295-319. Review. PubMed PMID: 10563973. 17: Robbins KR, Baker DH, Finley JW. Studies on the utilization of lysinoalanine and lanthionine. J Nutr. 1980 May;110(5):907-15. PubMed PMID: 6768858. 18: van Rooijen C, Bosch G, van der Poel AF, Wierenga PA, Alexander L, Hendriks WH. Quantitation of Maillard reaction products in commercially available pet foods. J Agric Food Chem. 2014 Sep 3;62(35):8883-91. doi: 10.1021/jf502064h. Epub 2014 Aug 20. PubMed PMID: 25088431. 19: Mechanism of toxicity of lysinoalanine. Nutr Rev. 1989 Nov;47(11):362-4. Review. PubMed PMID: 2513540. 20: Faist V, Müller C, Drusch S, Erbersdobler HF. Selective fortification of lysinoalanine, fructoselysine and N epsilon-carboxymethyllysine in casein model systems. Nahrung. 2001 Jun;45(3):218-21. PubMed PMID: 11455792.