Epsilon-polylysine Chemical Properties

Melting point:

172 °C

solubility 

DMSO (Slightly), Methanol (Slightly), Water (Slightly)

form 

Solid

color 

White to Pale Yellow

InChI

InChI=1/C8H18N2O/c1-3-4-5-6-7(9)8(11)10-2/h7H,3-6,9H2,1-2H3,(H,10,11)/t7-/s3

InChIKey

YLBHPLDJISPYOJ-KPOCXSGKNA-N

SMILES

C(NC)(=O)[C@@H](N)CCCCC |&1:4,r|

Epsilon-polylysine Usage And Synthesis

Description

ε-Polylysine is a light yellow powder with strong hygroscopicity and slightly bitter taste. It is a linear polymer of lysine. It is produced by streptomyces fermentation and has a broad-spectrum antibacterial effect. ε-polylysine is polymerized by 25-30 lysine groups, which is relatively stable to pH and heat. Its antibacterial effect is related to the degree of polymerization and the environment. The molecular weight of polylysine is between 3600-4300 which has the best antibacterial activity.

History

In 1977, Japanese scholars S. Shima and H. Sakai, in the process of screening Dragendo~Positive (DP) substances from microorganisms, discovered that a strain of actinomycete No.346 can produce a large amount of stable DP substances. The analysis and structural analysis of the hydrolysate confirmed that the DP substance is a homopolymer of 25-30 lysine residues. A homologous amino acid polymer formed by NH2 condensation, so it is called ε-Poly-L-lysine (ε-Poly-L-lysine for short ε-PL).

Physical properties

ε-PL pure product is light yellow powder, slightly bitter, strong hygroscopicity, and slightly bitter. It is easily soluble in water, slightly soluble in ethanol, but insoluble in organic solvents such as ethyl acetate and ether. It has high stability and antibacterial effect.

Safety

ε-PL enters the human body and is converted into lysine through digestion and decomposition. Lysine is one of the eight essential amino acids for the human body. It is an amino acid allowed to be added to food and is non-toxic and harmless to the human body. Therefore, ε -PL as a nutritional bacteriostatic agent, its safety is much higher than other chemical preservatives.

description

Epsilon-polylysine (ε-PL) is an antimicrobial commercially produced by Streptomyces fermentation and widely used in Asian countries for food preservation. epsilon-polylysine is approved for food use in Japan as an antimicrobial preservative.
Epsilon-polylysine (ε-PL) is a small cationic isopeptide made from the essential amino acid L-lysine. It exhibits antimicrobial activity against a wide spectrum of bacteria, yeast, and fungi and is heat stable and active in different food matrices. ε-PL has been a popular food preservative in Japan since the late 1980s, followed by Korea and China, and has been given Generally Regarded As Safe (GRAS) status in the USA. As a secondary metabolite, ε-PL was first discovered from the soil bacterium Streptomyces albulus, which is still used in its commercial production. Later, more producers of ε-PL were identified from the family of Streptomycetaceae, including the genera Streptomyces and Kitasatospora, and ergot fungi. ε-PL is synthesized by a cell-membrane-bound nonribosomal peptide synthetase (NRPS)-like enzyme named ε-PL synthetase (Pls).
Distribution of Epsilon-Polylysine Synthetases in Coryneform Bacteria Isolated from Cheese and Human Skin

chemical properties

Epsilon-polylysine is produced in Japan, and levels as low as 5 ppm have been found to be inhibitory, especially of some Gram-positive bacteria. It is water soluble, effective over a wide pH range, and is degraded to lysine by proteases.

ε-Polylysine

ε-Polylysine (ε-poly-L-lysine, EPL) is typically produced as a homopolypeptide of approximately 25–30 L-lysine residues.
Epsiliseen®- H is a natural antimicrobial agent with ultra-high concentration of E-Polylysine, used in food, cosmeceutical and pharmaceutical applications.
ε-Polylysine (ε-poly-L-lysine), the main active ingredient in Epsiliseen®, is a small polypeptide of the essential amino acid L-lysinethat is produced by bacterial fermentation; the natural fermentation is only observed in strains of bacteria in the genus Streptomyces.
ε-Polylysine is commercially used as a food preservative in Japan, the republic of Korea and in the USA. Food products containing polylysine are mainly found in Japan. The use of polylysine is common in food applications like: boiled rice, cooked vegetables, soups, noodles and sliced fish (sushi).

Chemical Properties

from Streptomyces albulus.

Uses

ε-Poly-L-lysine posess antimicrobial action stronger than alpha-Poly-L-lysine. Studies on the mode of action of ε-?PL suggest that adsorption of ε-?PL to the bacterial cell surface plays an important role in its antibacterial activity.

Definition

ChEBI: A macromolecule composed of repeating L-lysyl units joined via 1,6-amide linkages.

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