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Pyroglutamic acid

Pyroglutamic acid^[1]

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	C1CC(=O)NC1C(=O)O
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 disclaimer and 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]

References

^ Merck Index, 11th Edition, 8012.
^ 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:doi:10.1016/0006-291X(78)91646-7. PMID 26343.

v • d • e Protein primary structure and posttranslational modifications
General	Protein biosynthesis \| Peptide bond \| Proteolysis \| Racemization \| N-O acyl shift
N-terminus	Acetylation \| Formylation \| Pyroglutamate \| Methylation \| Glycation \| Myristoylation (Gly) \| carbamylation
C-terminus	Amidation \| Glycosyl phosphatidylinositol (GPI) \| O-methylation \| Glypiation \| Ubiquitination \| Sumoylation
Lysine	Methylation \| Acetylation \| Acylation \| Hydroxylation \| Ubiquitination \| SUMOylation \| Desmosine \| ADP-ribosylation \| Deamination and Oxidation to aldehyde
Cysteine	Disulfide bond \| Prenylation \| Palmitoylation
Serine/Threonine	Phosphorylation \| Glycosylation
Tyrosine	Phosphorylation \| Sulfation \| Porphyrin ring linkage \| Flavin linkage \| GFP prosthetic group (Thr-Tyr-Gly sequence) formation \| Lysine tyrosine quinone (LTQ) formation \| Topaquinone (TPQ) formation
Asparagine	Deamidation \| Glycosylation
Aspartate	Succinimide formation
Glutamine	Transglutamination
Glutamate	Carboxylation \| Polyglutamylation \| Polyglycylation
Arginine	Citrullination \| Methylation
Proline	Hydroxylation
←Amino acids Secondary structure→

Categories: Lactams | Carboxylic acids

This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Pyroglutamic_acid". A list of authors is available in Wikipedia.

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Pyroglutamic acid

References

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