Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Chemical compound
Pyroglutamic acid (also known as PCA, 5-oxoproline, pidolic acid) is a ubiquitous but understudied natural amino acid derivative in which the free amino group of glutamic acid or glutamine cyclizes to form a lactam.[1] The names of pyroglutamic acid conjugate base, anion, salts, and esters are pyroglutamate, 5-oxoprolinate, or pidolate.
Formation of pyroglutamic acid from N-terminal glutamine.
It is a metabolite in the glutathione cycle that is converted to glutamate by 5-oxoprolinase. Pyroglutamate is found in many proteins including bacteriorhodopsin. N-terminal glutamic acid and glutamine residues can spontaneously cyclize to become pyroglutamate, or enzymatically converted by glutaminyl cyclases.[2] This is one of several forms of blocked N-termini 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.[3]
Pyroglutamic acid exists as two distinct enantiomers:
(2R) or D which happens to be (+) or d
(2S) or L which happens to be (–) or l
^Cite error: The named reference throwing was invoked but never defined (see the help page).
^Schilling, Stephan; Wasternack, Claus; Demuth, Hans-Ulrich (1 August 2008). "Glutaminyl cyclases from animals and plants: a case of functionally convergent protein evolution". Biological Chemistry. 389 (8): 983–91. doi:10.1515/BC.2008.111. PMID 18979624. S2CID 24074284.
^Podell, David N.; Abraham, George N. (March 1978). "A technique for the removal of pyroglutamic acid from the amino terminus of proteins using calf liver pyroglutamate amino peptidase". Biochemical and Biophysical Research Communications. 81 (1): 176–185. doi:10.1016/0006-291X(78)91646-7. PMID 26343.
Pyroglutamicacid (also known as PCA, 5-oxoproline, pidolic acid) is a ubiquitous but understudied natural amino acid derivative in which the free amino...
amino acids and α-hydroxy acids (lactic acids) excreted from sweat; free fatty acids and amino acids from sebum; and urocanic acid and pyroglutamicacid. The...
Magnesium pidolate, the magnesium salt of pidolic acid (also known as pyroglutamicacid), is a mineral supplement, which contains 8.6% magnesium w/w....
ketoacidosis (a serious condition in which the body produces high levels of blood acids called ketones) after surgery, the FDA has approved changes to the prescribing...
neurotransmitter GABA and shares the same 2-oxo-pyrrolidone base structure with pyroglutamicacid. Related drugs include the anticonvulsants levetiracetam and brivaracetam...
has been chemically modified (e.g. by acetylation or formation of Pyroglutamicacid). Edman degradation is generally not useful to determine the positions...
converted to aspartic acid or isoaspartic acid. Glutamine is converted to glutamic acid or pyroglutamicacid (5-oxoproline). In a protein or peptide, these...
has the amino acid sequence pGlu-Pro-Ser-Lys-Asp-Ala-Phe-Ile-Gly-Leu-Met-NH2 (qPSKDAFIGLM-NH2) where pGlu and q stand for pyroglutamicacid. Like all tachykinin...
(trimethylaminoethanol), pyroglutamicacid, B vitamins, glucuronolactone, and DMAE (dimethylaminoethanol). These amino acids were claimed to have positive...
improve treatment outcomes. Paracetamol ester prodrug containing L-pyroglutamicacid (PGA), a biosynthetic precursor of glutathione, has been synthesized...
Quinolacetic acid is a metabolite associated with Hawkinsinuria. Hawkinsinuria--identification of quinolacetic acid and pyroglutamicacid during an acidotic...
phenylpiracetam, and all other members of the -racetam family, and also pyroglutamicacid. Malykh AG, Sadaie MR (February 2010). "Piracetam and piracetam-like...
acetylation or formation of pyroglutamicacid). Sequencing will stop if a non-α-amino acid is encountered (e.g. isoaspartic acid), since the favored five-membered...
excrete large amounts of a compound called 5-oxoproline (also called pyroglutamicacid, or pyroglutamate) in their urine (5-oxoprolinuria). This compound...
and B are 75 and 77 amino acid residues long, respectively, and each possess a seven-residue extension with a pyroglutamicacid post-translational modification...
presence of pyroglutamyl residues in many neuroendocrine peptides. The amino acid sequence of this enzyme is 86% identical to that of bovine glutaminyl cyclase...
Kishi and his co-workers, here they prepped an intermediate from L-pyroglutamicacid in 18 steps. Others have made it to the same intermediate in fewer...
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