L-Lysine Chemical Properties

Melting point:

215 °C (dec.)(lit.)

alpha 

D20 +14.6° (c = 6.5); D23 +25.9° (c = 2 in 6.0N HCl)

Boiling point:

265.81°C (rough estimate)

Density 

1.1360 (rough estimate)

FEMA 

3847 | L-LYSINE

refractive index 

26 ° (C=2, 5mol/L HCl)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

H₂O: 0.1 g/mL, clear, colorless

form 

Powder or Crystals

pka

2.16(at 25℃)

color 

White to light yellow

Odor

odorless

optical activity

[α]20/D +26.0±1.0°, c = 2% in 6 M HCl

Water Solubility 

Soluble in water. Insoluble in ethanol, ethyl ether, acetone, benzene and common neutral solvent.

Merck 

14,5636

JECFA Number

1439

BRN 

1722531

Stability:

Stable. Incompatible with strong oxidizing agents.

InChIKey

KDXKERNSBIXSRK-YFKPBYRVSA-N

LogP

-3.05

CAS DataBase Reference

56-87-1(CAS DataBase Reference)

NIST Chemistry Reference

Lysine(56-87-1)

EPA Substance Registry System

Lysine (56-87-1)

Safety Information

Hazard Codes 

Xi

Safety Statements 

24/25

WGK Germany 

3

RTECS 

OL5540000

TSCA 

Yes

HS Code 

29224110

Hazardous Substances Data

56-87-1(Hazardous Substances Data)

MSDS

• Language:English Provider:L-Lysine
• Language:English Provider:SigmaAldrich

L-Lysine Usage And Synthesis

Description

See ι-LYSINE MONOCHLORIDE.

Chemical Properties

L-Lysine is an essential amino acid (a protein building block) that cannot be produced by the body from other nutri ents. It helps ensure adequate absorption of calcium and the formation of collagen for bone, cartilage and connective tissue. This compound is odorless.

Chemical Properties

White to pale yellow crystalline powder

Occurrence

Some natural food sources for l-lysine include lima beans, kidney beans, potatoes, corn, red meat, fish and milk.

Uses

L-Lysine is an essential amino acid used in human nutrition. It plays a vital role in calcium absorption, building muscle protein and recovering from surgery or sports injuries. It is used for the treatment of herpes infections and cold sores. Its derivatives lysine acetylsalicylate is utilized to treat pain as well as to detoxify the body after heroin use. It is an important additive to animal feed. Further, it is used in many foods, especially red meats, fish and dairy products.

Uses

Essential amino acid for human development. Lysine residues are useful in many cellular processes, due to their ability to accept a wide variety of post-translational modifications.

Uses

lysine is a skin-conditioning amino acid.

Uses

A moderate serotonin antagonist and essential amino acid.

Definition

ChEBI: An L-alpha-amino acid; the L-isomer of lysine.

Preparation

Produced by fermentation. Also produced by use of continuous ion exchange technology.

Biotechnological Production

C. glutamicum and, to a lesser extent, E. coli are the main organisms used today for industrial L-lysine production. The first L-producing strains based on C. glutamicum were reported in 1961, and those based on E. coli in 1995. The advantages of using E. coli versus C. glutamicum include the achievement of higher growth rates at higher fermentation temperatures. The formation of lysine is highly influenced by two enzymes, aspartate kinase (AK) and homoserine dehydrogenase (HDH). AK converts aspartate into aspartate semialdehyde, and is highly feedback-inhibited by lysine and threonine. HDH converts aspartate semialdehyde into homoserine, which is an intermediate for the biosynthesis of threonine, methionine, and isoleucine. L-Lysine–producing strains therefore often contain a deregulated AK and/or a reduced activity HDH. Despite the improvement of the flux from aspartate towards lysine, the availability of key metabolites from the central metabolic pathways is also essential. Here the formation of oxaloacetate directly from phosphoenol pyruvate or via pyruvate is essential for the carbon yield as some unnecessary cycles are included. For example, inactivation of the enzyme phosphoenol pyruvate carboxykinase, which catalyzes the reverse reaction from oxaloacetate to phosphoenol pyruvate gave an improvement in lysine formation. By overexpression of pyruvate carboxylase, the conversion yield of glucose to lysine could be increased by 50 %. With a synthetic lysine hyperproducing strain, containing 12 defined modifications from the wild type, a carbon yield of 0.55 g/g and a product titer of 120 g/L over 30 h fermentation could be obtained.
Today, however, the main commercial process for L-lysine remains the fermentation of C. glutamicum. This is performed in fed-batch mode in large-scale fermenters of up to 500 m3 volume, with production capacities in excess of 100,000 tonnes. The commercial manufacturing process has been comprehensively described by Pfefferle.

Aroma threshold values

Detection: 500 ppm

Synthesis Reference(s)

Journal of the American Chemical Society, 71, p. 3161, 1949 DOI: 10.1021/ja01177a063

General Description

L-Lysine is a basic amino acid.

Safety Profile

An experimental teratogen. Experimental reproductive effects. When heated to decomposition it emits toxic fumes of NOx.

Veterinary Drugs and Treatments

Lysine may be effective in suppressing FHV-1 infections in cats.

Purification Methods

Crystallise L-lysine from aqueous EtOH. [Greenstein & Winitz The Chemistry of the Amino Acids J. Wiley, Vol 3 pp 2097-2122 1961, Kearley & Ingersoll J Am Chem Soc 73 5783 1951, Beilstein 4 IV 2717.]

L-Lysine(56-87-1)Related Product Information

• L-Lysine dihydrochloride
• Poly-L-lysine
• L-Lysine hydrochloride
• H-LYS-NH2 2HCL
• L-Phenylalanine
• L-Isoleucine
• L-Threonine
• L-Lysine S-(carboxymethyl)-L-cysteine
• Ethyl 2,6-diaminohexanoate dihydrochloride
• Methyl L-lysinate dihydrochloride
• L-Carnosine
• L-Malic acid
• L-Tyrosine
• L-Aspartic acid
• Methyl (S)-(-)-lactate
• L-Valine
• L-carnitine
• L-Glutamine