Information About

Histidine




  Name 2-amino-3-(3H-imidazol-4-yl)propanoic acid
  Abbreviations H, His
  C 6 H=9 N=3 O=2
  Mass 15516
  Melt Point 287
  Isoelectric Point 759
  Dissoc Constant 170<br/>604<br/>909
  CAS 351-50-8 (D), 71-00-1 (L)
  EINECS 206-513-8 (D) , 200-745-3 (L)
  PubChem 71083 (D) , 6274 (L)
  SMILES C1=C(NC=N1)CC(C(=O)O)N


Histidine is one of the 20 most common natural to the aromatic ring and as such is slighty Acidic , whereas the other one donates only one electron to the ring so it has a free lone pair and is Basic . These properties are exploited in different ways in proteins. In Catalytic Triad s, 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 Anhydrase s, 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.

The amino acid is a precursor for Histamine and Carnosine biosynthesis.

There are two Isoforms : D-histidine and L-histidine.


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