5746-04-3

Basic information

• Product Name: NE-CARBOXYMETHYL-L-LYSINE
• Synonyms: n(6)-carboxymethyllysine;NE-CARBOXYMETHYL-L-LYSINE;2-AMINO-6-(CARBOXYMETHYL-AMINO)-HEXANOIC ACID;CML;EPSILON-N-CARBOXYMETHYL-L-LYSINE;2-Amino-6-(carboxymethyk-amino)-hexanoic acid;N(EPSILON)-CARBOXYMETHYLLYSINE;CML, N-epsilon-Carboxymethyl-L-lysine
• CAS NO: 5746-04-3
• Molecular Formula: C₈H₁₆N₂O₄
• Molecular Weight: 204.22
• Product Categories: All Aliphatics;Aliphatics;Amino Acids & Derivatives
• Mol File: 5746-04-3.mol
• Article Data: 8

Chemical Properties

• Melting Point: 280°C (dec.)
• Boiling Point: 428.9 °C at 760 mmHg
• Flash Point: 213.2 °C
• Appearance: Off-white solid
• Density: 1.255 g/cm³
• Vapor Pressure: 1.47E-08mmHg at 25°C
• Refractive Index: 1.518
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Solubility: Water (Slightly, Heated, Sonicated)
• PKA: 2.35±0.10(Predicted)
• CAS DataBase Reference: NE-CARBOXYMETHYL-L-LYSINE(CAS DataBase Reference)
• NIST Chemistry Reference: NE-CARBOXYMETHYL-L-LYSINE(5746-04-3)
• EPA Substance Registry System: NE-CARBOXYMETHYL-L-LYSINE(5746-04-3)

Safety Data

• Hazardous Substances Data: 5746-04-3(Hazardous Substances Data)

Usage

Chemical Properties

Off-White Solid

Uses

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

Definition

ChEBI: An L-lysine derivative with a carboxymethyl substituent at the N6-position.

InChI:InChI=1/C8H16N2O4/c9-6(8(13)14)3-1-2-4-10-5-7(11)12/h6,10H,1-5,9H2,(H,11,12)(H,13,14)/t6-/m0/s1

Upstream product

• 19729-28-3 N^α-formyl-L-lysine 
• 50-99-7 D-glucose 
• 73-22-3 L-Tryptophan 
• 70-47-3 L-asparagine 
• 56-87-1 L-lysine 
• 131543-46-9 Glyoxal 
• 13734-28-6 Boc-Lys-OH 
• 1372658-92-8 (2S)-benzyl 6-{[(benzyloxy)-2-oxoethyl]amino}-2-{[(benzyloxy)carbonyl]amino}hexanoate 
• 1946-82-3 N-Ac-L-Lys-OH 
• 298-12-4 Glyoxilic acid 
• 71171-88-5 L-lysine formate 
• 123392-50-7 N^α-formyl,N^εcarboxymethyllysine 
• 64-69-7 Iodoacetic acid 
• 79-08-3 bromoacetic acid 

Downstream Products

• 56-87-1 L-lysine 
• 3158-42-7 (2-(2,4-dinitrophenyl)hydrazono)acetic 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.

Glucoselysine is derived from fructose and accumulates in the eye lens of diabetic rats

Prolonged hyperglycemia generates advanced glycation endproducts (AGEs), which are believed to be involved in the pathogenesis of diabetic complications. In the present study, we developed a polyclonal antibody against fructose-modified proteins (Fru-P antibody) and identified its epitope as glucoselysine (GL) by NMR and LC-electrospray ionization (ESI)- quadrupole TOF (QTOF) analyses and evaluated its potential role in diabetes sequelae. Although the molecular weight of GL was identical to that of fructoselysine (FL), GL was distinguishable from FL because GL was resistant to acid hydrolysis, which converted all of the FLs to furosine. We also detected GL in vitro when reduced BSA was incubated with fructose for 1 day. However, when we incubated reduced BSA with glucose, galactose, or mannose for 14 days, we did not detect GL, suggesting that GL is dominantly generated from fructose. LC-ESI-MS/MS experiments with synthesized [13C6]GL indicated that the GL levels in the rat eye lens time-dependently increase after streptozotocininduced diabetes. We observed a 31.3-fold increase in GL 8 weeks after the induction compared with nondiabetic rats, and N∈-(carboxymethyl)lysine and furosine increased by 1.7- and 21.5-fold, respectively, under the same condition. In contrast, sorbitol in the lens levelled off at 2 weeks after diabetes induction. We conclude that GL may be a useful biological marker to monitor and elucidate the mechanism of protein degeneration during progression of diabetes.

A kind of organic synthesis of carboxymethyl lysine separation and purification method

The invention provides a separating purification method of organically synthesized carboxy methyl lysine. Separating purification is a key step for finally obtaining high-purity carboxy methyl lysine; preparative liquid chromatography and ion exchange chromatography separating purification methods are used at present in the prior art and these methods are relatively cumbersome, low in efficiency and not suitable for mass preparation. To explore quick, efficient and low-price separating purification method becomes very important for obtaining a large quantity of low-cost high-purity carboxy methyl lysine monomers. The separating purification method of carboxy methyl lysine is innovated boldly in the invention, the synthesis amount of carboxy methyl lysine is improved to the gram grade, the purification efficiency of carboxy methyl lysine is increased greatly, the experiment cost is lowered, and a foundation is further laid for carrying out various toxicological evaluations on carboxy methyl lysine.