Lysine
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2008-07-05T17:12:43Z
Broeda
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/* External links */ removed links: first had multiple links, second was a down site, third was not even about lysine
{{NatOrganicBox
| image=<br>[[Image:L-lysine-skeletal.png|200px|Chemical structure of Lysine]]
[[Image:L-lysine-3D-sticks.png|180px|Chemical structure of Lysine]]
| name=2,6-diaminohexanoic acid
| PubChem = 866
| CAS = 56-87-1
| SMILES = C(CCN)CC(C(=O)O)N
| C=6 | H=14 | N=2 | O=2
| mass=146.188 g/mol
}}
'''Lysine''' (abbreviated as '''Lys''' or '''K''')<ref>{{cite web | author=IUPAC-IUBMB Joint Commission on Biochemical Nomenclature | title=Nomenclature and Symbolism for Amino Acids and Peptides | work=Recommendations on Organic & Biochemical Nomenclature, Symbols & Terminology etc | url=http://www.chem.qmul.ac.uk/iupac/AminoAcid/ | accessdate=2007-05-17}}</ref> is an α-[[amino acid]] with the [[chemical formula]] HO<sub>2</sub>CCH(NH<sub>2</sub>)(CH<sub>2</sub>)<sub>4</sub>NH<sub>2</sub>. This amino acid is an [[essential amino acid]], which means that humans cannot synthesize it. Its [[codon]]s are AAA and AAG.
Lysine is a [[basic (chemistry)|base]], as are [[arginine]] and [[histidine]]. The ε-amino group often participates in hydrogen bonding and as a general base in [[catalysis]]. Common [[posttranslational modification]]s include methylation of the ε-amino group, giving methyl-, dimethyl-, and trimethyllysine. The latter occurs in [[calmodulin]]. Other [[posttranslational modification]]s at lysine residues include [[acetylation]] and [[ubiquitination]]. [[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 (biology)|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 Δ<sup>1</sup>-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:<ref>Nelson, D. L.; Cox, M. M. "Lehninger, Principles of Biochemistry" 3rd Ed. Worth Publishing: New York, 2000. ISBN 1-57259-153-6.</ref>
# [[Aspartokinase]]
# β-aspartate semialdehyde [[dehydrogenase]]
# Dihydropicolinate [[synthase]]
# Δ<sup>1</sup>-piperidine-2,6-dicarboxylate dehydrogenase
# ''N''-succinyl-2-amino-6ketopimelate synthase
# Succinyl diaminopimelate [[aminotransferase]]
# Succinyl diaminopimelate desuccinylase
# Diaminopimelate [[epimerase]]
# Diaminopimelate [[decarboxylase]]
==Metabolism==
Lysine is [[Metabolism|metabolised]] in [[mammal]]s to give [[acetyl-CoA]], via an initial [[transamination]] with [[Ketoglutaric acid|α-ketoglutarate]]. The [[bacteria]]l degradation of lysine yields [[cadaverine]] by [[decarboxylation]].
==Synthesis==
Synthetic, racemic lysine has long been known.<ref>Braun, J. V. “Synthese des inaktiven Lysins aus Piperidin" Berichte der deutschen chemischen Gesellschaft 1909, Volume 42, p 839-846. DOI: 10.1002/cber.190904201134.</ref> A practical synthesis starts from [[caprolactam]].<ref>Eck, J. C.; Marvel, C. S. “dl-Lysine Hydrochlorides” Organic Syntheses, Collected Volume 2, p.374 (1943). http://www.orgsyn.org/orgsyn/pdfs/CV2P0374.pdf</ref>
==Dietary sources==
The human [[Nutrition|nutritional requirement]] is 1–1.5 g daily. It is the [[Essential_amino_acid#Use_of_essential_amino_acids|limiting amino acid]] (the essential amino acid found in the smallest quantity in the particular foodstuff) in all [[cereal grain]]s, but is plentiful in all [[Pulse (legume)|pulses]] (legumes). Plants that contain significant amounts of lysine include:{{Fact|date=June 2007}}
*[[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|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.
*[[Lupin|White Lupin]] (19,330–21,585 ppm) in seed.
*[[Caraway|Black Caraway]], [[Black cumin|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.
==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.<ref name=Griffith2>
{{cite journal
| author=Griffith RS, Norins AL, Kagan C. | title=A multicentered study of lysine therapy in Herpes simplex infection | journal=Dermatologica. | year=1978 | pages=257–267 | volume=156 | issue=5 | pmid=640102
}}</ref> However, more research is needed to fully substantiate this claim. For more information, refer to [[Herpes#Lysine|Herpes simplex - Lysine]].
There are Lysine conjugates that show promise in the treatment of [[cancer]], by causing cancerous cells to destroy themselves when the drug is combined with the use of [[Light therapy|phototherapy]], while leaving non-cancerous cells unharmed.<ref name=lysineconjugates>
{{cite web | author=ScienceDaily | title=Chemists Kill Cancer Cells With Light-activated Molecules | url=http://www.sciencedaily.com/releases/2007/08/070808132019.htm | accessdate=2008-01-24}}
</ref>
==In popular culture==
The 1993 film ''[[Jurassic Park (film)|Jurassic Park]]'', which is based on the 1989 [[Michael Crichton]] novel ''[[Jurassic Park]]'', features [[dinosaur]]s that were [[Genetic engineering|genetically altered]] so they could not produce lysine.<ref>{{cite news | last = Coyne | first = Jerry A. | coauthors = | title = The Truth Is Way Out There | work = [[The New York Times]] | pages = | language = | publisher = | date = [[October 10]] [[1999]] | url = http://query.nytimes.com/gst/fullpage.html?res=9E0DE6D7153EF933A25753C1A96F958260 | accessdate = 2008-04-06 }}</ref> This was supposed to prevent the [[Cloning|cloned]] dinosaurs from leaving the park, forcing them to depend on lysine supplements provided by the park's veterinary staff. Most [[vertebrate]]s cannot produce lysine by default (it is an [[essential amino acid]]).
The 2002 [[Max Tundra]] single "Lysine" (featuring Becky Jacobs) is a tribute to the advantages of lysine.<ref>{{cite web | last = | first = | authorlink = | coauthors = | title = Lysine (CDep) | work = Insound | publisher = | date = | url = http://www.insound.com/search/showrelease.jsp?p=INS15613 | format = | doi = | accessdate = 2008-04-06 }}</ref>
The [[India]]n children's vitamin tonic, ''Incremin'', was claimed to supply this essential amino acid.
==References==
<references/>
==See also==
*[[Acetyllysine]]
*[[Lysine price-fixing conspiracy]]
*[[Deamination]]
*[[Saccharopine]]
==Sources==
*Much of the information in this article has been translated from [[:de:Lysin|German Wikipedia]].
*{{RubberBible83rd}}
==External links==
{{AminoAcids}}
[[Category:Proteinogenic amino acids]]
[[Category:Ketogenic amino acids]]
[[Category:Basic amino acids]]
[[Category:Essential amino acids]]
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