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Chemical structure of Lysine

Chemical structure of Lysine

Lysine

Systematic (IUPAC) name
2,6-diaminohexanoic acid
Identifiers
CAS number56-87-1
PubChem        866
Chemical data
FormulaC6H14N2O2 
Molar mass146. IUPAC Nomenclature is a system of naming Chemical compounds and of describing the science of Chemistry in general CAS registry numbers are unique numerical identifiers for Chemical compounds Polymers biological sequences mixtures and Alloys They are also referred to PubChem is a Database of chemical Molecules The system is maintained by the National Center for Biotechnology Information (NCBI a component A chemical formula is a way of expressing information about the Atoms that constitute a particular Chemical compound, and how the relationship between those atoms changes Carbon (kɑɹbən is a Chemical element with the symbol C and its Atomic number is 6 Hydrogen (ˈhaɪdrədʒən is the Chemical element with Atomic number 1 Nitrogen (ˈnaɪtɹəʤɪn is a Chemical element that has the symbol N and Atomic number 7 and Atomic weight 14 Oxygen (from the Greek roots ὀξύς (oxys (acid literally "sharp" from the taste of acids and -γενής (-genēs (producer literally begetteris the Molar mass, symbol M, is the Mass of one mole of a substance ( Chemical element or Chemical compound) 188 g/mol
SMILESC(CCN)CC(C(=O)O)N
Complete data

Lysine (abbreviated as Lys or K)[1] is an α-amino acid with the chemical formula HO2CCH(NH2)(CH2)4NH2. In Chemistry, an amino acid is a Molecule containing both Amine and Carboxyl Functional groups In Biochemistry, this A chemical formula is a way of expressing information about the Atoms that constitute a particular Chemical compound, and how the relationship between those atoms changes This amino acid is an essential amino acid, which means that humans cannot synthesize it. An essential amino acid or indispensable amino acid is an Amino acid that cannot be synthesized de novo by the organism (usually referring to Its codons are AAA and AAG. The genetic code is the set of rules by which information encoded in genetic material ( DNA or RNA sequences is translated into Proteins

Lysine is a base, as are arginine and histidine. In Chemistry, a base is most commonly thought of as an aqueous substance that can accept Protons This refers to the Brønsted-Lowry theory of acids and Arginine (abbreviated as Arg or R) is an α- Amino acid. The L-form is one of the 20 most common natural amino acids Histidine (abbreviated as His or H) is one of the 20 standard Amino acids present in Proteins In the Nutritional sense in The ε-amino group often participates in hydrogen bonding and as a general base in catalysis. Catalysis is the process in which the rate of a Chemical reaction is increased by means of a Chemical substance known as a catalyst Common posttranslational modifications include methylation of the ε-amino group, giving methyl-, dimethyl-, and trimethyllysine. Posttranslational modification (PTM is the chemical modification of a Protein after its translation. The latter occurs in calmodulin. Calmodulin ( CaM) (an abbreviation for CAL cium MODUL ated prote' IN') is a calcium-binding protein expressed in all Eukaryotic cells Other posttranslational modifications include acetylation. Posttranslational modification (PTM is the chemical modification of a Protein after its translation. Acetylation (or in IUPAC nomenclature ethanoylation) describes a reaction that introduces an Acetyl Functional group into an Organic compound Collagen contains hydroxylysine which is derived from lysine by lysyl hydroxylase. Collagen is the main Protein of Connective tissue in Animals and the most abundant protein in Mammals making up about 50% of the whole-body protein 5-Hydroxylysine is an Amino acid with the molecular formula C6H14N2O3 Lysyl hydroxylase (or procollagen-lysine 5-dioxygenase) is an Oxygenase Enzyme which catalyzes the Hydroxylation of Lysine to O-Glycosylation of lysine residues in the endoplasmic reticulum or Golgi apparatus is used to mark certain proteins for secretion from the cell. Glycosylation is the enzymatic process that links Saccharides to produce glycans, either free or attached to Proteins and Lipids This enzymatic The endoplasmic reticulum (Greek endo = "within" (prefix plásma = "formed entity" Latin reticulum = "little net" or ER, is an Organelle The Golgi apparatus (also called the Secretion is the process of segregating elaborating and releasing chemicals from a cell, or a secreted Chemical substance or amount of substance The cell is the structural and functional unit of all known living Organisms It is the smallest unit of an organism that is classified as living and is often called

Contents

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. Aspartic acid (abbreviated as Asp or D; Asx or B represent either aspartic acid or Asparagine) is an α- Amino acid 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. Pimelic acid is the Organic compound with the formula HO2C(CH25CO2H Enzymes involved in this biosynthesis include:[2]

  1. Aspartokinase
  2. β-aspartate semialdehyde dehydrogenase
  3. Dihydropicolinate synthase
  4. Δ1-piperidine-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. Aspartokinase (or Aspartate kinase is an Enzyme that catalyzes the Phosphorylation of the Amino acid Aspartate. A dehydrogenase is an Enzyme that Oxidizes a substrate by transferring one or more Protons and a pair of electrons to an acceptor usually In Biochemistry, a synthase is an Enzyme which Catalyzes a Synthesis process In Biochemistry, a transaminase or an aminotransferase is an Enzyme that Catalyzes a type of reaction between an Amino acid and an Epimerases and racemases are Isomerase Enzymes that catalyze the inversion of Stereochemistry in biological molecules Carboxy-lyases, also known as decarboxylases, are carbon-carbon Lyases that add or remove a Carboxyl group from Organic compounds These Metabolism is the set of Chemical reactions that occur in living Organisms in order to maintain Life. Mammals ( class Mammalia) are a class of Vertebrate Animals characterized by the presence of Sweat glands, including sweat glands Acetyl-CoA is an important molecule in metabolism used in many biochemical reactions There are two chemical reactions known as transamination (or aminotransfer Alpha-ketoglutaric acid is one of two Ketone derivatives of Glutaric acid. The bacterial degradation of lysine yields cadaverine by decarboxylation. The Bacteria ( singular: bacterium) are a large group of unicellular Microorganisms Typically a few Micrometres in length bacteria have Cadaverine is a foul-smelling molecule produced by Protein Hydrolysis during Putrefaction of animal tissue Decarboxylation is any Chemical reaction in which a Carboxyl group (-COOH is split off from a compound as Carbon dioxide (CO2

Synthesis

Synthetic, racemic lysine has long been known. [3] A practical synthesis starts from caprolactam. Caprolactam is an Organic compound which is a Lactam of 6-aminohexanoic acid (ε-aminohexanoic acid Aminocaproic acid) [4]

Dietary sources

The human nutritional requirement is 1–1. Nutrition (also called nourishment or aliment) is the provision to cells and Organisms of the materials necessary (in the form of food to support 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). An essential amino acid or indispensable amino acid is an Amino acid that cannot be synthesized de novo by the organism (usually referring to Pulses are annual leguminous crops yielding from one to twelve Grains or Seeds of variable size shape and color within a Pod, according Plants that contain significant amounts of lysine include:

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. Amaranthus, collectively known as amaranth or pigweed, is a cosmopolitan genus of herbs For the town with a similar name see Quinua Peru. "Quinoa" is also a title of a 1992 music album by Tangerine Dream.

Properties

L-Lysine is a necessary building block for all protein in the body. Proteins are large Organic compounds made of Amino acids arranged in a linear chain and joined together by Peptide bonds between the Carboxyl 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. Calcium (ˈkælsiəm is the Chemical element with the symbol Ca and Atomic number 20 Muscle (from Latin musculus, diminutive of mus "mouse" is contractile tissue of the body and is derived from the Surgery (from the χειρουργική cheirourgikē, via chirurgiae meaning "hand work" is a medical specialty that uses operative manual and instrumental Hormones (from Greek ὁρμή - "impetus" are chemicals released by cells that affect cells in other parts of the body Enzymes are Biomolecules that catalyze ( ie increase the rates of Chemical reactions Almost all enzymes are Proteins Antibodies (also known as immunoglobulins, abbreviated Ig) are Gamma globulin Proteins that are found in Blood or other Bodily

Clinical significance

It has been suggested that lysine may be beneficial for those with herpes simplex infections. [5] However, more research is needed to fully substantiate this claim. For more information, refer to Herpes simplex - Lysine. Herpes simplex is a Viral disease caused by Herpes simplex viruses both herpes simplex virus 1 (HSV-1 and herpes simplex virus 2 (HSV-2 cause herpes simplex

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 phototherapy, while leaving non-cancerous cells unharmed. Cancer (medical term Malignant Neoplasm) is a class of Diseases in which a group of cells display uncontrolled Light therapy or phototherapy consists of exposure to daylight or to specific wavelengths of light using Lasers, LEDs Fluorescent lamps, [6]

In popular culture

The 1993 film Jurassic Park, which is based on the 1989 Michael Crichton novel Jurassic Park, features dinosaurs that were genetically altered so they could not produce lysine. Jurassic Park is a 1993 Science fiction film directed by Steven Spielberg and based on the novel of the same name by Michael John Michael Crichton, ˈkraɪtən, (born October 23 1942 is an American author Film producer, Film director, Medical doctor, and Television producer Jurassic Park is a Science fiction Novel that was written by Michael Crichton and published in 1990. Genetic engineering, Recombinant DNA technology, genetic modification/manipulation (GM and gene splicing are terms that apply to the direct [7] This was supposed to prevent the cloned dinosaurs from leaving the park, forcing them to depend on lysine supplements provided by the park's veterinary staff. Cloning in Biology is the process of producing populations of genetically-identical individuals that occurs in nature when organisms such as Bacteria, Insects Most vertebrates cannot produce lysine by default (it is an essential amino acid). Vertebrates are members of the Subphylum Vertebrata, Chordates with backbones or spinal columns The grouping sometimes includes An essential amino acid or indispensable amino acid is an Amino acid that cannot be synthesized de novo by the organism (usually referring to

The 2002 Max Tundra single "Lysine" (featuring Becky Jacobs) is a tribute to the advantages of lysine. Ben Jacobs, more commonly known by the Stage name Max Tundra, is an English-born musican [8]

The Indian children's vitamin tonic, Incremin, was claimed to supply this essential amino acid. India, officially the Republic of India (भारत गणराज्य inc-Latn Bhārat Gaṇarājya; see also other Indian languages) is a country

References

  1. ^ IUPAC-IUBMB Joint Commission on Biochemical Nomenclature. Nomenclature and Symbolism for Amino Acids and Peptides. Recommendations on Organic & Biochemical Nomenclature, Symbols & Terminology etc. Retrieved on 2007-05-17. Year 2007 ( MMVII) was a Common year starting on Monday of the Gregorian calendar in the 21st century. Events 1521 - Edward Stafford 3rd Duke of Buckingham, is executed for Treason.
  2. ^ Nelson, D. L. ; Cox, M. M. "Lehninger, Principles of Biochemistry" 3rd Ed. Worth Publishing: New York, 2000. ISBN 1-57259-153-6.
  3. ^ 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.
  4. ^ 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
  5. ^ Griffith RS, Norins AL, Kagan C. (1978). "A multicentered study of lysine therapy in Herpes simplex infection". Dermatologica. 156 (5): 257-267. PMID 640102.  
  6. ^ ScienceDaily. Chemists Kill Cancer Cells With Light-activated Molecules. Retrieved on 2008-01-24. 2008 ( MMVIII) is the current year in accordance with the Gregorian calendar, a Leap year that started on Tuesday of the Common Events 41 - Gaius Caesar (Caligula, known for his eccentricity and cruel Despotism, is Assassinated by his disgruntled
  7. ^ Coyne, Jerry A. . "The Truth Is Way Out There", The New York Times, October 10, 1999. Events 680 - Battle of Karbala: Shia Imam Husayn bin Ali, the grandson of the Prophet Muhammad, is decapitated Year 1999 ( MCMXCIX) was a Common year starting on Friday (link will display full 1999 Gregorian calendar) Retrieved on 2008-04-06. 2008 ( MMVIII) is the current year in accordance with the Gregorian calendar, a Leap year that started on Tuesday of the Common Events 46 BC - Julius Caesar defeats Caecilius Metellus Scipio and Marcus Porcius Cato in the Battle of Thapsus  
  8. ^ Lysine (CDep). Insound. Retrieved on 2008-04-06. 2008 ( MMVIII) is the current year in accordance with the Gregorian calendar, a Leap year that started on Tuesday of the Common Events 46 BC - Julius Caesar defeats Caecilius Metellus Scipio and Marcus Porcius Cato in the Battle of Thapsus

See also

Sources

External links

Dictionary

lysine

-noun

  1. (biochemistry) An essential amino acid C6H14N2O2 found in most animal proteins; essential for growth especially in children.
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