(2S, 1'R)/(2S, 1'S)-2-Amino-6-(1'-carboxy-ethylamino)-he xanoic acid Chemical Properties

Boiling point:

427.7±45.0 °C(Predicted)

Density 

1?+-.0.06 g/cm3(Predicted)

solubility 

Water: Slightly Soluble

form 

A solid

pka

2.30±0.10(Predicted)

(2S, 1'R)/(2S, 1'S)-2-Amino-6-(1'-carboxy-ethylamino)-he xanoic acid Usage And Synthesis

Description

N^ε-(1-Carboxyethyl)-L-lysine (CEL) is an advanced glycation end product (AGE) produced by the reaction of methyl glyoxal with lysine residues in proteins. Protein bound, but not free, CEL binds to the receptor for AGEs (RAGE). CEL levels are elevated in the lens of diabetic patients with cataract. Long-term caloric restriction decreases CEL levels in rat heart mitochondria. It decreases glutamate uptake and secretion of S100B in rat hippocampal slices in a RAGE-independent manner when used at a concentration of 1 mM.

Uses

CEL and CML are two stable, nonenzymatic chemical modifications of protein lysine residues resulting from glycation and oxidation reactions.

Definition

ChEBI: N(6)-(1-carboxyethyl)-L-lysine is a L-lysine derivative formed during the reaction between methylglyoxal and protein. CEL is a homologue of N(epsilon)-(carboxymethyl)lysine (CML), an advanced glycation end-product that is formed on reaction of glyoxal or glycolaldehyde with protein and on oxidative cleavage of fructoselysine, the Amadori adduct formed on glycation of protein by glucose. It is a L-lysine derivative and a non-proteinogenic L-alpha-amino acid.

References

[1] M U AHMED. N-epsilon-(carboxyethyl)lysine, a product of the chemical modification of proteins by methylglyoxal, increases with age in human lens proteins.[J]. Biochemical Journal, 1997, 324 ( Pt 2): 565-570. DOI: 10.1042/bj3240565
[2] JING XUE. The Receptor for Advanced Glycation End Products (RAGE) Specifically Recognizes Methylglyoxal-Derived AGEs[J]. Biochemistry Biochemistry, 2014, 53 20: 3327-3335. DOI: 10.1021/bi500046t
[3] ZEHRA HASHIM  Shamshad Z. Advanced glycation end products in diabetic and non-diabetic human subjects suffering from cataract.[J]. AGE, 2011: 377-384. DOI: 10.1007/s11357-010-9177-1
[4] G. JANSEN J K P Hollman. Aging increases Nepsilon-(carboxymethyl)lysine and caloric restriction decreases Nepsilon-(carboxyethyl)lysine and Nepsilon-(malondialdehyde)lysine in rat heart mitochondrial proteins.[J]. Free Radical Research, 1900, 90 1: 47-54. DOI: 10.1080/10715760210165
[5] FERNANDA HANSEN. Methylglyoxal and carboxyethyllysine reduce glutamate uptake and S100B secretion in the hippocampus independently of RAGE activation[J]. Amino Acids, 2015, 48 2: 375-385. DOI: 10.1007/s00726-015-2091-1

(2S, 1'R)/(2S, 1'S)-2-Amino-6-(1'-carboxy-ethylamino)-he xanoic acid(5746-03-2)Related Product Information

• NE-CARBOXYMETHYL-L-LYSINE
• (2S, 1'R)/(2S, 1'S)-2-Amino-6-(1'-carboxy-ethylamino)-he xanoic acid
• 2-Carboxyethyl acrylate
• LYSINE THIAZOLIDINE CARBOXYLATE