ChemicalBook > CAS DataBase List > (2S, 1'R)/(2S, 1'S)-2-Amino-6-(1'-carboxy-ethylamino)-he xanoic acid

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

Product Name
(2S, 1'R)/(2S, 1'S)-2-Amino-6-(1'-carboxy-ethylamino)-he xanoic acid
CAS No.
5746-03-2
Chemical Name
(2S, 1'R)/(2S, 1'S)-2-Amino-6-(1'-carboxy-ethylamino)-he xanoic acid
Synonyms
CEL (>70% purity);Carboxyethyllysine;Loratadine Impurity 71;Nε-(Carboxyethyl)lysine;N-6-(Carboxyethyl)-L-lysine;N(6)-(1-carboxyethyl)lysine;Nε-(1-Carboxyethyl)-L-lysine;L-Lysine, N6-(1-carboxyethyl)-;N-[(5S)-5-amino-5-carboxypentyl]-DL-alanine;(2S)-2-amino-6-(1-carboxyethylamino)hexanoic acid
CBNumber
CB51112970
Molecular Formula
C9H18N2O4
Formula Weight
218.25
MOL File
5746-03-2.mol
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(2S, 1'R)/(2S, 1'S)-2-Amino-6-(1'-carboxy-ethylamino)-he xanoic acid Property

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)
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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Cayman Chemical
Product number
25333
Product name
Nε-(1-Carboxyethyl)-L-lysine
Purity
≥95%
Packaging
1mg
Price
$37
Updated
2024/03/01
Cayman Chemical
Product number
25333
Product name
Nε-(1-Carboxyethyl)-L-lysine
Purity
≥95%
Packaging
5mg
Price
$161
Updated
2024/03/01
Cayman Chemical
Product number
25333
Product name
Nε-(1-Carboxyethyl)-L-lysine
Purity
≥95%
Packaging
10mg
Price
$301
Updated
2024/03/01
TRC
Product number
C178070
Product name
Nε-(1-Carboxyethyl)-L-lysine(MixtureofDiastereomers)
Packaging
10mg
Price
$160
Updated
2021/12/16
AK Scientific
Product number
9212DA
Product name
N(6)-(1-Carboxyethyl)-L-lysine
Packaging
1mg
Price
$139
Updated
2021/12/16
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(2S, 1'R)/(2S, 1'S)-2-Amino-6-(1'-carboxy-ethylamino)-he xanoic acid Chemical Properties,Usage,Production

Description

Nε-(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 Preparation Products And Raw materials

Raw materials

Preparation Products

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

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5746-03-2, (2S, 1'R)/(2S, 1'S)-2-Amino-6-(1'-carboxy-ethylamino)-he xanoic acidRelated Search:

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

  • N(6)-(1-carboxyethyl)lysine
  • CEL (>70% purity)
  • Nε-(1-Carboxyethyl)-L-lysine
  • Nμ-(1-Carboxyethyl)-L-lysine\n(Mixture of Diastereomers)
  • (2S, 1'R)/(2S, 1'S)-2-Amino-6-(1'-carboxy-ethylamino)-he xanoic acid
  • L-Lysine, N6-(1-carboxyethyl)-
  • N-6-(Carboxyethyl)-L-lysine
  • (2S)-2-amino-6-(1-carboxyethylamino)hexanoic acid
  • N-[(5S)-5-amino-5-carboxypentyl]-DL-alanine
  • Nε-(1-Carboxyethyl)-L-lysine_x000b_(Mixture of Diastereomers)
  • Nε-(Carboxyethyl)lysine
  • Carboxyethyllysine
  • Loratadine Impurity 71
  • NEpsilon-(1-carboxyethyl)-L-lysine(Mixture of Diastereomers)
  • 5746-03-2