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Chemical Compound Review

Pyroglutamate     5-oxopyrrolidine-2-carboxylic acid

Synonyms: PubChem9493, SureCN15791, CHEMBL284718, AG-D-96299, Proline,5-oxo-, ...
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Disease relevance of Pidolic acid

  • 5-Oxoprolinuria (pyroglutamic aciduria) resulting from glutathione synthetase (GSS) deficiency is an inherited autosomal recessive disorder characterized, in its severe form, by massive urinary excretion of 5-oxoproline, metabolic acidosis, haemolytic anaemia and central nervous system damage [1].
  • The mechanism of biosynthesis of NH2-terminal pyroglutamic acid has been studied in a mouse plasmacytoma (RPC-20) which produces an immunoglobulin light (lambda) chain containing NH2-terminal pyroglutamic acid [2].
  • (3S,5S)-Carbapenam carboxylic acid was prepared from L-pyroglutamic acid to unambiguously establish its absolute configuration as identical to the natural product isolated from Serratia marcescens and from overexpression of the biosynthetic genes carAB in Escherichia coli [3].
  • In additional studies of salicylic acid (SA) and pyroglutamic acid (PGA), the hands of volunteers were contaminated with rhinovirus at defined times after application of the acid, and then volunteers attempted to inoculate the nasal mucosa with one hand and quantitative viral cultures were done on the other hand [4].
  • The reagents in the five kits designed to detect the enzyme pyroglutamic acid arylamidase in Streptococcus pyogenes reacted positively with S. pyogenes (group A streptococcus); however, the reagents also reacted positively with all group D enterococcal streptococci and with about half of the staphylococcal strains treated [5].

Psychiatry related information on Pidolic acid


High impact information on Pidolic acid

  • Amino acid sequence following removal of N-terminal pyroglutamate is presented [10].
  • Physalaemin and tumor peptide had similar retention times on high-performance liquid chromatography after chemical and enzymic modifications that included pH changes, oxone oxidation, use of a hydrophilic ion-pairing reagent, and digestion with trypsin and pyroglutamate aminopeptidase [11].
  • The extracellular domain of CLAC-P/collagen type XXV was secreted by furin convertase, and the N-terminus of CLAC deposited in AD brains was pyroglutamate modified [12].
  • Crystal structures of human glutaminyl cyclase, an enzyme responsible for protein N-terminal pyroglutamate formation [13].
  • The short chains of gNa and gNa' and of BngNAP1 and BngNAP1' differ by the replacement of N-terminal proline by pyroglutamic acid; the long chains of gNaA and BngNAP1B contain a six amino acid stretch, MQGQQM, which is present in gNa (according to its DNA sequence) but absent from BngNAP1 and BngNAP1C [14].

Chemical compound and disease context of Pidolic acid


Biological context of Pidolic acid


Anatomical context of Pidolic acid


Associations of Pidolic acid with other chemical compounds


Gene context of Pidolic acid

  • By a combination of Edman degradation and mass spectrometry, it was established that GDCF-2 comprises 76 amino acid residues, commencing at the N terminus with pyroglutamic acid [35].
  • Cyclization of Gln1 to form pyroglutamate (pE) limited the site of cross-linking in the mutant to Lys45, permitting identification of receptor residues that are proximal to this residue of bound EGF [36].
  • Although a few structures of CC chemokines have been reported, none of these was determined with the N-terminal pyroglutamic acid residue (pGlu1) and a complete C-terminus. pGlu1 is essential for the chemotactic activity of MCP-2 [37].
  • To analyze the postsecretory processing of Abeta, we used the same in vivo paradigm and showed that Abeta1-40 and Abeta1-42 were processed at their N termini to yield variants starting at pyroglutamate, and at their C termini to yield variants ending at Val40 and at Val39 [38].
  • The results demonstrate that the structure of the predominant relaxin in human semen plasma is derived from the product of the H2 gene, consisting of a N-terminal pyroglutamic acid A-24 A chain and a mixture of B-26 and B-27 B chains [39].

Analytical, diagnostic and therapeutic context of Pidolic acid

  • The complete primary structure of aphrodisin was determined by sequence analysis of intact aphrodisin after unblocking the amino terminus with pyroglutamate aminopeptidase and from peptides generated by trypsin and Lys-C digests [40].
  • Fast atom bombardment mass spectrometry (FABMS) was used to demonstrate that the amino-terminal residues of peptides 25-60, and 25-90 are pyroglutamic acid, a modification which precludes Edman degradation of these peptides [41].
  • Titrations of each component by the other suggest that phosphorylated 5-oxoproline-bound Component A is the entity that interacts with Component B [42].
  • The amino acid sequences were determined by automated Edman degradation following proteolytic digestion of the isolated proteins and HPLC separation of the resulting fragments and by amino-terminal sequencing after treatment with pyroglutamate aminopeptidase [43].
  • The MALDI in-source decay measurements combined with nanoESI (nanoelectrospay ionization) MS/MS measurements obtained after specific proteolysis of SBP, allowed the exact positioning of a single N-linked carbohydrate group, and the identification of a pyroglutamate residue at the sequence N-terminus [44].


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  20. Study of the 5-oxoprolinase reaction by 13C NMR. Li, L.Y., Seddon, A.P., Meister, A., Inubushi, T. J. Biol. Chem. (1989) [Pubmed]
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  24. Purification and characterization of a unique, potent, peptidyl probe for the high conductance calcium-activated potassium channel from venom of the scorpion Buthus tamulus. Galvez, A., Gimenez-Gallego, G., Reuben, J.P., Roy-Contancin, L., Feigenbaum, P., Kaczorowski, G.J., Garcia, M.L. J. Biol. Chem. (1990) [Pubmed]
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  28. Formation of N-pyroglutamyl peptides from N-Glu and N-Gln precursors in Aplysia neurons. Garden, R.W., Moroz, T.P., Gleeson, J.M., Floyd, P.D., Li, L., Rubakhin, S.S., Sweedler, J.V. J. Neurochem. (1999) [Pubmed]
  29. Toxicity of pyroglutaminated amyloid beta-peptides 3(pE)-40 and -42 is similar to that of A beta1-40 and -42. Tekirian, T.L., Yang, A.Y., Glabe, C., Geddes, J.W. J. Neurochem. (1999) [Pubmed]
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