Lysine

Lysine
IUPAC name	2,6-diaminohexanoic acid
Other names	Lys, K
Identifiers
CAS number	[56-87-1]
PubChem	866
EINECS number	200-294-2
MeSH	Lysine
SMILES	C(CCN)CC(C(=O)O)N
Properties
Molecular formula	C6H14N2O2
Molar mass	146.188
Melting point	224 °C
Acidity (pKa)	2.15, 9.16, 10.67
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)

Lysine is an α-amino acid with the chemical formula HO₂CCH(NH₂)(CH₂)₄NH₂. Its three letter code is Lys, its one letter code is K, and its codons are AAA and AAG. This amino acid is essential amino acid, which means that humans cannot synthesise it. Lysine is a basic, as are arginine and histidine. The ε-amino group often participates in hydrogen bonding and as a general base in catalysis.

Common posttranslational modifications include methylation of the e-amino group, giving methyl-, dimethyl-, and trimethyllysine. The latter occurs in calmodulin. Other posttranslational modifications include acetylation. Collagen contains hydroxylysine which is derived from lysine by lysyl hydroxylase. O-Glycosylation of lysine residues in the endoplasmic reticulum or Golgi apparatus is used to mark certain proteins for secretion from the cell.

Biosynthesis

As an essential amino acid, lysine is not synthesized in animals, hence it must be ingested as lysine or lysine-containing proteins. In plants and microorganisms, it is synthesized from aspartic acid, which is first converted to β-aspartyl-semialdehyde. Cyclization gives dihydropicolinate, which is reduced to Δ¹-piperidine-2,6-dicarboxylate. Ring-opening of this heterocycle gives a series of derivatives of pimelic acid, ultimately affording lysine. Enzymes involves in this biosynthesis include:

1. aspartokinase
2. β-aspartate semialdehyde dehydrogenase
3. dihydropicolinate synthase
4. Δ¹-piperdine-2,6-dicarboxylate dehydrogenase
5. N-succinyl-2-amino-6ketopimelate synthase
6. succinyl diaminopimelate aminotransferase
7. succinyl diaminopimelate desuccinylase
8. diaminopimelate epimerase
9. diaminopimelate decarboxylase

Metabolism

Lysine is metabolised in mammals to give acetyl-CoA, via an initial transamination with α-ketoglutarate. The bacterial degradation of lysine yields cadaverine by decarboxylation.

Synthesis

Synthetic, racemic lysine has long been known. A practical synthesis starts from caprolactam.

Dietary sources

The human nutritional requirement is 1–1.5 g daily. Used as a dietary supplement. It is the limiting amino acid in all cereal grains, but is plentiful in all pulses (legumes). Fish are also quite rich in lysine. Plants that contain significant amounts of lysine include:^{[citation needed]}

• Buffalo Gourd (10,130–33,000 ppm) in seed
• Berro, Watercress (1,340–26,800 ppm) in herb.
• Soybean (24,290–26,560 ppm) in seed.
• Carob, Locust Bean, St.John's-Bread (26,320 ppm) in seed;
• Common Bean (Black Bean, Dwarf Bean, Field Bean, Flageolet Bean, French Bean, Garden Bean, Green Bean, Haricot, Haricot Bean, Haricot Vert, Kidney Bean, Navy Bean, Pop Bean, Popping Bean, Snap Bean, String Bean, Wax Bean) (2,390–25,700 ppm) in sprout seedling;
• Ben Nut, Benzolive Tree, Jacinto (Sp.), Moringa (aka Drumstick Tree, Horseradish Tree, Ben Oil Tree), West Indian Ben (5,370–25,165 ppm) in shoot.
• Lentil (7,120–23,735 ppm) in sprout seedling.
• Asparagus Pea, Winged Bean (aka Goa Bean) (21,360–23,304 ppm) in seed.
• Fat Hen (3,540–22,550 ppm) in seed.
• Lentil (19,570–22,035 ppm) in seed.
• White Lupin (19,330–21,585 ppm) in seed.
• Black Caraway, Black Cumin, Fennel-Flower, Nutmeg-Flower, Roman Coriander (16,200–20,700 ppm) in seed.
• Spinach (1,740–20,664 ppm).
• Amaranth, Quinoa

Properties

L-Lysine is a necessary building block for all protein in the body. L-Lysine plays a major role in calcium absorption; building muscle protein; recovering from surgery or sports injuries; and the body's production of hormones, enzymes, and antibodies.

Clinical significance

It has been suggested that lysine may be beneficial for those with herpes simplex infections. However, more research is needed to fully substantiate this claim. For more information, refer to Herpes simplex - Lysine.

Lysine can help to alleviate the symptoms of coldsores. They help to speed up the healing process if taken immediately.

See also

• Acetyllysine
• Lysine price-fixing conspiracy
• Deamination
• Saccharopine

References

• Much of the information in this article has been translated from German Wikipedia.
• Template:RubberBible83rd

• Longe, J. L. 2006. The Gale Encyclopedia of Medicine. Detroit: Thomson Gale. ISBN 1414403682.

• Bender, D. A., and A. E. Bender. 2005. A Dictionary of Food and Nutrition. New York: Oxford University Press. ISBN 0198609612.

External links

• Lysine biosynthesis (early stages), Lysine biosynthesis (later stages), and Lysine catabolism at Queen Mary, University of London
• Computational Chemistry Wiki at compchemwiki.org
• L-Lysine at PDRhealth.com

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