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MedKoo Cat#: 597573 | Name: Lysinoalanine, (S,S)-

Description:

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

Lysinoalanine, (S,S)- is a toxic compound in processed proteinaceous foods.

Chemical Structure

Lysinoalanine, (S,S)-
Lysinoalanine, (S,S)-
CAS#23250-50-2

Theoretical Analysis

MedKoo Cat#: 597573

Name: Lysinoalanine, (S,S)-

CAS#: 23250-50-2

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 #
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Synonym
Lysinoalanine, (S,S)-; N6-Lysino-L-alanine; Lysine, N6-(2-amino-2-carboxyethyl)-, L,L-;
IUPAC/Chemical Name
N6-((S)-2-amino-2-carboxyethyl)-L-lysine
InChi Key
IMSOBGJSYSFTKG-BQBZGAKWSA-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](CCCCNC[C@H](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

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.

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: 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. 2: Pintauro SJ, Philippossian G, Finot PA, Lee TC. Lysinoalanine: absence of mutagenic response in the Salmonella/mammalian-microsome mutagenicity assay. Food Chem Toxicol. 1985 Aug;23(8):763-5. PubMed PMID: 3930353. 3: 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. 4: Friedman M. Lysinoalanine in food and in antimicrobial proteins. Adv Exp Med Biol. 1999;459:145-59. Review. PubMed PMID: 10335374. 5: Pfaender P. Lysinoalanine--a toxic compound in processed proteinaceous foods. World Rev Nutr Diet. 1983;41:97-109. Review. PubMed PMID: 6428067. 6: 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. 7: 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. 8: 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. 9: 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. 10: Boschin G, D'Agostina A, Rinaldi A, Arnoldi A. Lysinoalanine content of formulas for enteral nutrition. J Dairy Sci. 2003 Jul;86(7):2283-7. PubMed PMID: 12906044. 11: Pfaff G. Lysinoalanine contents of formula diets. Lancet. 1984 Feb 25;1(8374):448. PubMed PMID: 6142167. 12: Chang HM, Tsai CF, Li CF. Changes of amino acid composition and lysinoalanine formation in alkali-pickled duck eggs. J Agric Food Chem. 1999 Apr;47(4):1495-500. PubMed PMID: 10564005. 13: Bosch L, Sanz ML, Montilla A, Alegría A, Farré R, del Castillo MD. Simultaneous analysis of lysine, Nepsilon-carboxymethyllysine and lysinoalanine from proteins. J Chromatogr B Analyt Technol Biomed Life Sci. 2007 Dec 1;860(1):69-77. Epub 2007 Oct 22. PubMed PMID: 17997368. 14: Montilla A, Gómez-Ruiz JA, Olano A, del Castillo MD. A GC-FID method for analysis of lysinoalanine. Mol Nutr Food Res. 2007 Apr;51(4):415-22. PubMed PMID: 17390402. 15: Boschin G, Scaglioni L, Arnoldi A. Optimization of the synthesis of the cross-linked amino acid ornithinoalanine and nuclear magnetic resonance characterization of lysinoalanine and ornithinoalanine. J Agric Food Chem. 1999 Mar;47(3):939-44. PubMed PMID: 10552395. 16: Fujimoto D, Hirama M, Iwashita T. Occurrence of lysinoalanine in calcified tissue collagen. Biochem Biophys Res Commun. 1981 Dec 31;103(4):1378-83. PubMed PMID: 6800379. 17: Savoie L. Effect of protein treatment on the enzymatic hydrolysis of lysinoalanine and other amino acids. Adv Exp Med Biol. 1984;177:413-22. PubMed PMID: 6437165. 18: Linetsky M, Hill JM, LeGrand RD, Hu F. Dehydroalanine crosslinks in human lens. Exp Eye Res. 2004 Oct;79(4):499-512. PubMed PMID: 15381034. 19: Walsh RG, Nashef AS, Feeney RE. Intramolecular cross-linking of proteins by formation of lysinoalanine or lanthionine. Modification of disulfides in ovomucoids. Int J Pept Protein Res. 1979 Oct;14(4):290-9. PubMed PMID: 521212. 20: Zarkadas CG, Zarkadas GC, Karatzas CN, Khalili AD, Nguyen Q. Rapid method for determining desmosine, isodesmosine, 5-hydroxylysine, tryptophan, lysinoalanine and the amino sugars in proteins and tissues. J Chromatogr. 1986 May 28;378(1):67-76. PubMed PMID: 3090084.