5746-03-2

Basic information

• Product Name: (2S, 1'R)/(2S, 1'S)-2-Amino-6-(1'-carboxy-ethylamino)-he xanoic acid
• Synonyms: (2S, 1'R)/(2S, 1'S)-2-Amino-6-(1'-carboxy-ethylamino)-he xanoic acid;N(6)-(1-carboxyethyl)lysine;CEL (>70% purity) ;Nε-(1-Carboxyethyl)-L-lysine;Nμ-(1-Carboxyethyl)-L-lysine\n(Mixture of Diastereomers)
• CAS NO: 5746-03-2
• Molecular Formula: C₉H₁₈N₂O₄
• Molecular Weight: 436.502
• Mol File: 5746-03-2.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 427.7±45.0 °C(Predicted)
• Appearance: /
• Density: 1 +-.0.06 g/cm3(Predicted)
• PKA: 2.30±0.10(Predicted)
• CAS DataBase Reference: (2S, 1'R)/(2S, 1'S)-2-Amino-6-(1'-carboxy-ethylamino)-he xanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (2S, 1'R)/(2S, 1'S)-2-Amino-6-(1'-carboxy-ethylamino)-he xanoic acid(5746-03-2)
• EPA Substance Registry System: (2S, 1'R)/(2S, 1'S)-2-Amino-6-(1'-carboxy-ethylamino)-he xanoic acid(5746-03-2)

Safety Data

• Hazardous Substances Data: 5746-03-2(Hazardous Substances Data)

Usage

Description

(2S, 1'R)/(2S, 1'S)-2-Amino-6-(1'-carboxy-ethylamino)-hexanoic acid, also known as Nε-(1-Carboxyethyl)-L-lysine (CEL), is an advanced glycation end product (AGE) formed by the reaction of methyl glyoxal with lysine residues in proteins. It is protein-bound and can bind to the receptor for AGEs (RAGE). CEL is associated with various health conditions, including elevated levels in the lens of diabetic patients with cataracts and its effects on glutamate uptake and secretion of S100B in rat hippocampal slices.

Uses

Used in Medical Research:
(2S, 1'R)/(2S, 1'S)-2-Amino-6-(1'-carboxy-ethylamino)-hexanoic acid is used as a biomarker for [identifying and studying the progression of diabetic cataracts] because its elevated levels are found in the lens of diabetic patients with cataract.
Used in Nutritional Studies:
CEL is used as a research compound for [investigating the effects of caloric restriction] as it has been shown that long-term caloric restriction decreases CEL levels in rat heart mitochondria.
Used in Neurobiological Research:
(2S, 1'R)/(2S, 1'S)-2-Amino-6-(1'-carboxy-ethylamino)-hexanoic acid is used as a neurochemical agent for [studying the impact of AGEs on glutamate uptake and S100B secretion] in rat hippocampal slices, as it has been demonstrated to decrease glutamate uptake and secretion of S100B in a RAGE-independent manner when used at a concentration of 1 mM.

Upstream product

• 56-87-1 L-lysine 
• 50-99-7 D-glucose 
• 70-47-3 L-asparagine 
• 73-22-3 L-Tryptophan 

Downstream Products

• 56-87-1 L-lysine 
• 790-12-5 2-(2,4-dinitrophenylhydrazono)-propanoic acid 

Relevant articles and documents

Simultaneous generation of acrylamide, β-carboline heterocyclic amines and advanced glycation ends products in an aqueous Maillard reaction model system

The simultaneous formation of acrylamide; β-carboline heterocyclic amines (HAs): harmane and norharmane; and advanced glycation end products (AGEs) (Nε-(carboxymethyl)lysine (CML) and Nε-(carboxyethyl)lysine (CEL)) was analyzed based on an aqueous model system. The model systems included lysine–glucose (Lys/Glu), asparagine–glucose (Asn/Glu), tryptophan–glucose (Trp/Glu), and a mixture of these amino acids (Mix/Glu). Only AGEs were generated when heated at 100 °C, Asn and Trp competed with Lys for glucose and methylglyoxal (MGO), and glyoxal (GO) decreased AGE content. The k value of CML, CEL, and acrylamide decreased when heated at 130 °C, whereas that of harmane increased in the Mix/Glu, owing to the competition between Lys and Asn for glucose, GO, and MGO. Harmane preferably formed via the Pictet–Spengler condensation between Trp and acetaldehyde, which further reduced acrylamide formation via the acrolein pathway.