21291-40-7

Basic information

• Product Name: fructosyl-lysine
• Synonyms: fructosyl-lysine;ε-N-Deoxyfructosyllysine;ε-N-Deoxyfructosyllysine Dihydrochloride
• CAS NO: 21291-40-7
• Molecular Formula: C₁₂H₂₄N₂O₇
• Molecular Weight: 308.33
• Product Categories: Amines, Amino Acids & Derivatives, Carbohydrates & Derivatives
• Mol File: 21291-40-7.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 654.5°Cat760mmHg
• Flash Point: 349.6°C
• Appearance: /
• Density: 1.386g/cm³
• Vapor Pressure: 6.65E-20mmHg at 25°C
• Refractive Index: 1.564
• Storage Temp.: Hygroscopic, Refrigerator, Under Inert Atmosphere
• Solubility: Methanol (Slightly, Heated), Water (Slightly, Sonicated)
• PKA: 2.50±0.24(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: fructosyl-lysine(CAS DataBase Reference)
• NIST Chemistry Reference: fructosyl-lysine(21291-40-7)
• EPA Substance Registry System: fructosyl-lysine(21291-40-7)

Safety Data

• Hazardous Substances Data: 21291-40-7(Hazardous Substances Data)

Usage

Description

Fructosyl-lysine is a glyco-amino acid consisting of a D-fructosyl residue attached to the epsilon-amino group of L-lysine. It is a sugar-amino acid with potential antioxidant and anti-inflammatory properties.

Uses

Used in Pharmaceutical Industry:
Fructosyl-lysine is used as a pharmaceutical agent for its potential antioxidant and anti-inflammatory properties.
Used in Food Industry:
Fructosyl-lysine is used as a Maillard reaction product, which contributes to the color, flavor, and aroma of cooked and processed foods.
Used in Biotechnology Industry:
Fructosyl-lysine is used as a fructosyl-amino acid oxidase-reactive compound in fungal cells, which can be utilized for the development of new biotechnological applications.

InChI:InChI=1/C12H24N2O7/c13-7(12(20)21)3-1-2-4-14-5-8(16)10(18)11(19)9(17)6-15/h7,9-11,14-15,17-19H,1-6,13H2,(H,20,21)/t7-,9-,10-,11-/m1/s1

Synthetic route

Nα-formyl-L-lysine (19729-28-3) + D-glucose (50-99-7) → fructoselysine (21291-40-7)

Conditions	Yield
(i), (ii) aq. HCl; Multistep reaction;

L-lysine (56-87-1) + D-glucose (50-99-7) → fructoselysine (21291-40-7)

Conditions	Yield
In methanol at 65℃; for 4h;

fructoselysine (21291-40-7) + ATP (56-65-5) → fructose-lysine-3-phosphate (211359-11-4)

Conditions	Yield
With kinase at 37℃; for 2h;

fructoselysine (21291-40-7) → (2S)-2-amino-6-[(carboxymethyl)amino]hexanoate (55593-17-4, 5746-04-3)

Conditions	Yield
With dihydrogen peroxide; iron(II) chloride In aq. phosphate buffer at 37℃; for 1h; pH=7.2;

fructoselysine (21291-40-7) → ε-(2-furoylmethyl)-L-lysine (19746-33-9)

Conditions	Yield
With hydrogenchloride In water at 100℃; for 4h;

Upstream product

• 56-87-1 L-lysine 
• 50-99-7 D-glucose 
• 19729-28-3 N^α-formyl-L-lysine 

Downstream Products

• 55593-17-4 (2S)-2-amino-6-[(carboxymethyl)amino]hexanoate 
• 19746-33-9 ε-(2-furoylmethyl)-L-lysine 

Relevant articles and documents

An inhibitor of hyperglycemia containing Lysinyl-Fructose(LF) and a method manufacturing the same

The present invention relates to a method to manufacture Lysinyl-Fructose (LF), an in vitro inhibition activity of LF, manufactured by the method, on rat intestinal andalpha;-glucosidase, porcine pancreatic andalpha;-amylase, rat intestinal sucrase, rat intestinal maltase, and rat intestinal glucoamylase, and an in vivo inhibition activity on starch and sucrose degradation. Accordingly, LF manufactured by the method may be used to prevent and treat diabetes and to prevent diabetic complications.COPYRIGHT KIPO 2019