2-oxo-pyrrolidine carboxylic acid

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Pyroglutamic acid1
IUPAC name 5-oxopyrrolidine-2-carboxylic acid
Other names Pyrrolidonecarboxylic Acid, Pidolic acid, Pyroglutamate, 5-oxoproline
Identifiers
CAS number 98-79-3
PubChem 499
SMILES
 
Properties
Molecular formula C5H7NO3
Molar mass 129.114
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox references

Pyroglutamic acid, or pidolic acid, is an uncommon amino acid derivative in which the free amino group of glutamic acid cyclizes to form a lactam. It is found in many proteins including bacteriorhodopsin. N-terminal glutamine residues can spontaneously cyclize to become pyroglutamate. This is one of several forms of blocked N-terminals which present a problem for N-terminal sequencing using Edman chemistry, which requires a free primary amino group not present in pyroglutamic acid. The enzyme pyroglutamate aminopeptidase can restore a free N-terminus by cleaving off the pyroglutamate residue.2

Uses

It is sold, over the counter, as a "smart drug" for improving blood circulation in the brain.

Neutralizing pyroglutamic acid with sodium bicarbonate in water results in NaPCA, the compound human skin uses to retain moisture.citation needed

References

  1. ^ Merck Index, 11th Edition, 8012.
  2. ^ Podell DN, Abraham GN (March 15, 1978). "A technique for the removal of pyroglutamic acid from the amino terminus of proteins using calf liver pyroglutamate amino peptidase". Biochem. Biophys. Res. Commun. 81 (1): 176–85. doi:10.1016/0006-291X(78)91646-7. PMID 26343. 
v • d • e
Protein primary structure and posttranslational modifications
General
N terminus
C terminus
Lysine
Cysteine
Serine/Threonine
Tyrosine
Asparagine
Aspartate
Glutamine
Glutamate
Arginine
Proline

Wikipedia content modification information:

  • This page was last modified on 16 September 2008, at 11:18.

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