Lysine

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Lysine
Systematic (IUPAC) name
2,6-diaminohexanoic acid
Identifiers
CAS number	56-87-1
PubChem	866
Chemical data
Formula	C6H14N2O2
Molar mass	146.188 g/mol
SMILES	C(CCN)CC(C(=O)O)N
Complete data

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Lysine (abbreviated as Lys or K)^[1] is an α-amino acid with the chemical formula HO₂CCH(NH₂)(CH₂)₄NH₂. This amino acid is an essential amino acid, which means that humans cannot synthesize it. Its codons are AAA and AAG.

Lysine is a base, 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 ε-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 involved in this biosynthesis include:^[1]

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.^[1] A practical synthesis starts from caprolactam.^[1]

Dietary sources

The human nutritional requirement is 1–1.5 g daily. It is the limiting amino acid (the essential amino acid found in the smallest quantity in the particular foodstuff) in all cereal grains, but is plentiful in all pulses (legumes). Plants that contain significant amounts of lysine include:

• 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

Good sources of lysine are foods rich in protein including meat (specifically red meat, pork, and poultry), cheese (particularly parmesan), certain fish (such as cod and sardines), and eggs.

Nuts are particularly a bad source for lysine.#REDIRECT [[3]]

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.^[1] 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.

Trivia

In the movie Jurassic Park the dinosaurs were genetically altered so they could not produce lysine (the "lysine contingency"). This was supposed to prevent the dinosaurs from leaving the park.

References

See also

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

Sources

• Much of the information in this article has been translated from German Wikipedia.
• Lide, D. R. (ed.) (2002). CRC Handbook of Chemistry and Physics, 83rd ed., Boca Raton, FL: CRC Press. 

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

v • d • e Major families of biochemicals
Peptides | Amino acids | Nucleic acids | Carbohydrates | Nucleotide sugars | Lipids | Terpenes | Carotenoids | Tetrapyrroles | Enzyme cofactors | Steroids | Flavonoids | Alkaloids | Polyketides | Glycosides
Analogues of nucleic acids:	The 20 Common Amino Acids ("dp" = data page)	Analogues of nucleic acids:
Alanine (dp) | Arginine (dp) | Asparagine (dp) | Aspartic acid (dp) | Cysteine (dp) | Glutamic acid (dp) | Glutamine (dp) | Glycine (dp) | Histidine (dp) | Isoleucine (dp) | Leucine (dp) | Lysine (dp) | Methionine (dp) | Phenylalanine (dp) | Proline (dp) | Serine (dp) | Threonine (dp) | Tryptophan (dp) | Tyrosine (dp) | Valine (dp)

ar:ليسين

bn:লাইসিন ca:Lisina cs:Lysin de:Lysineo:Lizino fr:Lysine ko:리신 hr:Lizin id:Lisin it:Lisina he:ליזין lv:Lizīns lb:Lysin lt:Lizinas hu:Lizin nl:Lysine ja:リシンfi:Lysiini sv:Lysinuk:Лізин

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Acknowledgement and Attribution Regarding Sources of Content

Some of the initial content on this page may be incorporated in part from copyleft sources in the public domain including wikis such as Wikipedia and AskDrWiki. Drug information for patients came from the The National Library of Medicine. Infectious disease information may have come from the Centers for Disease Control (CDC). Differential Diagnoses are drawn from clinicians as well as an amalgamation of 3 sources: 1.The Disease Database; 2. Kahan, Scott, Smith, Ellen G. In A Page: Signs and Symptoms. Malden, Massachusetts: Blackwell Publishing, 2004:3; 3. Sailer, Christian, Wasner, Susanne. Differential Diagnosis Pocket. Hermosa Beach, CA: Borm Bruckmeir Publishing LLC, 2002:7 .