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Imidazole is incorporated into many important biological compounds. The most pervasive is the amino acid histidine, which has an imidazole side-chain. Histidine is present in many proteins and enzymes, e.g. by binding metal cofactors, as seen in hemoglobin. Imidazole-based histidine compounds play an important role in intracellular buffering. [17]
Histidine ball and stick model spinning. Histidine (symbol His or H) [2] is an essential amino acid that is used in the biosynthesis of proteins.It contains an α-amino group (which is in the protonated –NH 3 + form under biological conditions), a carboxylic acid group (which is in the deprotonated –COO − form under biological conditions), and an imidazole side chain (which is partially ...
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Histamine has two basic centres, namely the aliphatic amino group and whichever nitrogen atom of the imidazole ring does not already have a proton. Under physiological conditions, the aliphatic amino group (having a pK a around 9.4) will be protonated, whereas the second nitrogen of the imidazole ring (pK a ≈ 5.8) will not be protonated. [11]
Imidazole is the side chain of histidine and is typically used at a concentration of 150 - 500 mM for elution. Histidine or histamine can also be used. Decrease in pH; When the pH decreases, the histidine residue is protonated and can no longer coordinate the metal tag, allowing the protein to be eluted.
English: Top row: L-Histidine, D-Histidine and DL (or RS)-Histidine. Bottom row: same but with the alternative 3H tautomer in the imidazole ring. Bottom row: same but with the alternative 3H tautomer in the imidazole ring.
In nature, imidazole alkaloids are found both as secondary plant compounds and as byproducts of histidine metabolism in marine organisms. One well-known imidazole alkaloid is pilocarpine , which is present in the leaves of Paraguay jaborandi .