Lysine

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Lysine [1]
Systematic name (S)-2,6-Diaminohexanoic acid
Abbreviations Lys
K
Chemical formula C6H14N2O2
Molecular mass 146.19 g/mol
PubChem 876
Melting point 224 °C
Specific rotation +14.6°
Isoelectric point 9.74
pKa 2.15
9.16
10.67
CAS number [56-87-1]
EINECS number 200-294-2
SMILES NCCCCC(N)C(=O)O
Chemical structure of LysineChemical structure of Lysine
Disclaimer and references

Lysine is one of the 20 amino acids normally found in proteins. With its 4-aminobutyl (primary amine) side-chain, it is classified as a basic amino acid, along with arginine and histidine. It is an essential amino acid, and the human nutritional requirement is 1–1.5 g daily. As a dietary supplement, it is claimed that lysine may be useful for those with herpes simplex infections; however, the evidence regarding these benefits is mixed.

Contents

[edit] Dietary sources

Lysine 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:

  • Buffalo Gourd (10,130–33,000 ppm) in seed work
  • 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

[edit] 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.

Lysine Formula
Lysine Formula

Lysine can undergo posttranslational modification in protein molecules, often by methylation or acetylation. Collagen contains hydroxylysine which is derived from lysine. O-Glycosylation of lysine residues in the endoplasmic reticulum or Golgi apparatus is used to mark certain proteins for secretion from the cell.

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.

It has been suggested that lysine may be beneficial for those with herpes simplex infections.[2] However, more research is needed to fully substantiate this claim. For more information, refer to Herpes simplex - Lysine.

[edit] References

  1. ^ Merck Index, 12th Edition, 5667.
  2. ^ Griffith RS, Norins AL, Kagan C. (1978). "A multicentered study of lysine therapy in Herpes simplex infection". Dermatologica. 156 (5): 257-267. PMID 640102. 

[edit] See also

[edit] 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 Edn.). Boca Raton (FL):CRC Press. ISBN 0-8493-0483-0. 

[edit] External links


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Major Families of Biochemicals
Peptides | Amino acids | Nucleic acids | Carbohydrates | Lipids | Terpenes | Carotenoids | Tetrapyrroles | Enzyme cofactors | Steroids | Flavonoids | Alkaloids | Polyketides | Glycosides
Analogues of nucleic acids: The 20 Common Amino Acids 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)
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