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histidine

  (hĭs'tĭ-dēn', -dĭn) pronunciation
n.

An essential amino acid, C6H9N3O2, important for the growth and repair of tissues.

[HIST(O)– + –ID(E) + –INE2.]


 
 

An essential amino acid with a basic side chain.

 
Food and Fitness: histidine

An amino acid. Histidine was once thought to be an essential nutrient only for infants and children. Since 1975, it has been recognized as essential for adults as well.

 
Dental Dictionary: histidine

n

One of the essential amino acids for infants and children. See also amino acid.

 

One of the essential amino acids, first isolated in 1896. It occurs abundantly in hemoglobin and can be isolated from blood cells. It is used in medicine and biochemical research and as a dietary supplement and feed additive.

For more information on histidine, visit Britannica.com.

 

An essential amino acid in the diet of both adults and infants.

 
(hĭs'tĭdēn) , organic compound, one of the 22 α-amino acids commonly found in animal proteins. Only the L-stereoisomer appears in mammalian protein. Histidine is the direct precursor of histamine; it is also an important source of carbon atoms in the synthesis of purines. The imidazole group on the side chain of histidine can act as both an acid and a base, i.e., it can both donate and accept protons under some conditions. This turns out to be an important property when histidine is incorporated into proteins, particularly when it becomes a part of the primary structure of some enzymes. It is thought that the side chain of this amino acid acts as a general acid and base as it participates in the catalytic functions of chymotrypsin, as well as those of a number of enzymes dealing with the metabolism of carbohydrates, proteins, and nucleic acids. It has even been implicated in the workings of cocoonase, the enzyme that allows adult silk moths to escape from their cocoons. Histidine is considered to be an essential amino acid for infants (it must be supplied in the diet); experiments with adults indicate that they can go for at least short periods without dietary intake of this amino acid. It was isolated from protein in 1896; its structure was confirmed by chemical synthesis in 1911.


 

His; a naturally occurring amino acid, essential for optimal growth of the young; its decarboxylation results in formation of histamine.

 
Wikipedia: histidine

Chemical structure of Histidine

Chemical structure of Histidine

Histidine

Systematic (IUPAC) name
2-amino-3-(3H-imidazol-4-yl)propanoic acid
Identifiers
CAS number 71-00-1
PubChem         773
Chemical data
Formula C6H9N3O2 
Molar mass 155.16 g/mol
SMILES N[C@@H](Cc1[nH]cnc1)C(O)=O
Complete data

Histidine (abbreviated as His or H)[1] is one of the 20 most common natural amino acids present in proteins. In the nutritional sense, in humans, histidine is considered an essential amino acid, but mostly only in children. Its codons are CAU and CAC.

Histidine was first isolated in 1896 by German physician Albrecht Kossel.

Chemical properties

The imidazole side chains and the relatively neutral pKa of histidine (ca 6.0) mean that relatively small shifts in cellular pH will change its charge. For this reason, this amino acid side chain finds its way into considerable use as a coordinating ligand in metalloproteins, and also as a catalytic site in certain enzymes. The imidazole side chain has two nitrogens with different properties: One is bound to hydrogen and donates its lone pair to the aromatic ring and as such is slighty acidic, whereas the other one donates only one electron pair to the ring so it has a free lone pair and is basic. These properties are exploited in different ways in proteins. In catalytic triads, the basic nitrogen of histidine is used to abstract a proton from serine, threonine or cysteine to activate it as a nucleophile. In a histidine proton shuttle, histidine is used to quickly shuttle protons, it can do this by abstracting a proton with its basic nitrogen to make a positively-charged intermediate and then use another molecule, a buffer, to extract the proton from its acidic nitrogen. In carbonic anhydrases, a histidine proton shuttle is utilized to rapidly shuttle protons away from a zinc-bound water molecule to quickly regenerate the active form of the enzyme.

Metabolism

The amino acid is a precursor for histamine and carnosine biosynthesis.

Conversion of histidine to histamine by histidine decarboxylase
Enlarge
Conversion of histidine to histamine by histidine decarboxylase

The enzyme histidine ammonia-lyase converts histidine into ammonia and urocanic acid. A deficiency in this enzyme is present in the rare metabolic disorder histidinemia.

Additional images

References

    External links


    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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    Dictionary. The American Heritage® Dictionary of the English Language, Fourth Edition Copyright © 2007, 2000 by Houghton Mifflin Company. Updated in 2007. Published by Houghton Mifflin Company. All rights reserved.  Read more
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    Wikipedia. This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Histidine" Read more

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