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Pyroglutamate 5-oxopyrrolidine-2-carboxylic acid
Synonyms: PubChem9493, SureCN15791, CHEMBL284718, AG-D-96299, Proline,5-oxo-, ...
Facklam, R.R., Turner, R.B. et al., Gehrig, P.M. et al., Chaurand, P. et al., Shi, Z.Z. et al., et al.
Turner, Biedermann, Morgan, Keswick, Ertel, Barker, Boja, Hoodbhoy, Fales, Dean,
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].
The majority of amyloid beta peptide (Abeta) deposited in the brains of Alzheimer's disease (AD) patients is N-truncated, especially Abeta starting with pyroglutamate at position 3 (Abeta(3(pE))) [6].
Striatal deficiency of L-pyroglutamic acid in Huntington's disease is accompanied by increased plasma levels [7].
Pyroglutamic acid (PCA) was compared with placebo in a randomized, double blind trial for assessing its efficacy in treating memory deficits in 40 aged subjects [8].
Capillary electrophoresis for caffeine and pyroglutamate determination in coffees study of the in vivo effect on learning and locomotor activity in mice [9].
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].
We determined two crystal structures of G5K from Escherichia coli, at 2.9 A and 2.5 A resolution, complexed with glutamate and sulphate, or with G5P, sulphate and the proline analogue 5-oxoproline [15].
The presence of N-acetyl aspartic acid and 5-oxoproline exclusively in serous cystadenoma samples is remarkable [16].
Monosodium glutamate and its cyclization product, pyroglutamate, may provoke edema and associated symptoms [17].
An infant in this family presented with metabolic acidosis and excreted quinolacetic acid and pyroglutamic acid in the urine together with the tyrosine derived phenolic acids reported in the original index case [18].
Excessive excretion of 5-oxoproline and decreased levels of blood glutathione in type II diabetes mellitus [19].
The findings support the view that the coupling of ATP hydrolysis to 5-oxoproline decyclization involves formation of a phosphorylated tetrahedal intermediate [20].
The N termini of ZP1 and ZP3, but not ZP2, were blocked by cyclization of glutamine to pyroglutamate [21].
The post-translational modification, glutamate to pyroglutamate, was not present in soluble circulating ADan [22].
The findings are consistent with (but do not prove) the hypothesis that the Component A catalyzes an initial step in the reaction which involves 5-oxoproline and ATP, such as phosphorylation of 5-oxoproline [23].
IbTX displays 68% sequence homology with charybdotoxin (ChTX), another scorpion-derived peptidyl inhibitor of PK,Ca, and, like this latter toxin, its amino terminus contains a pyroglutamic acid residue [24].
This reaction is thought to be catalyzed by a pyroglutamate forming enzyme located within the secretory granule fraction [25].
The stability of lysosomal membranes to synthetic L-pyroglutamic acid, L-pyroglutamyl-L-alanine, L-pyroglutamyl-L-proline, and to selected fractions of the enzymic digests was tested [26].
Pyroglutamate-modified amyloid beta-peptides--AbetaN3(pE)--strongly affect cultured neuron and astrocyte survival [27].
The pGlu peptides are detected in isolated cell bodies, regenerated neurites in culture, interganglionic connective nerves, cell homogenates, and collected releasates [28].
An N-terminal truncated isoform of the amyloid beta-peptide (A beta) that begins with a pyroglutamate (pE) residue at position 3 [A beta3(pE)-42] is the predominant isoform found in senile plaques [29].
Partial amino-acid sequence of the precursor of an immunoglobulin light chain containing NH2-terminal pyroglutamic acid [30].
Characterization of a pyroglutamate aminopeptidase from rat serum that degrades thyrotropin-releasing hormone [31].
Edman sequencing and mass spectrometry of the purified ligands revealed two decapentapeptides, which differ only by an N-terminal pyroglutamate/glutamine [32].
5-Oxo-L-prolinase, an enzyme that catalyzes the conversion of 5-oxo-L-proline (L-pyroglutamate; L-2-pyrrolidone-5-carboxylate) to L-glutamate coupled with the cleavage of ATP to ADP and Pi, has been purified about 1600-fold from rat kidney [33].
The 29-kDa domain has a blocked NH2-terminal (pyrrolidone carboxylic acid) which was removed by digestion with pyroglutamate aminopeptidase, and the amino acid sequence of the first 36 residues was obtained [34].
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].
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].
Mutations in the glutathione synthetase gene cause 5-oxoprolinuria. Shi, Z.Z., Habib, G.M., Rhead, W.J., Gahl, W.A., He, X., Sazer, S., Lieberman, M.W. Nat. Genet. (1996) [Pubmed]
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Generation of amyloid beta peptide with pyroglutamate at position 3 in primary cortical neurons. Shirotani, K., Tsubuki, S., Lee, H.J., Maruyama, K., Saido, T.C. Neurosci. Lett. (2002) [Pubmed]
Striatal deficiency of L-pyroglutamic acid in Huntington's disease is accompanied by increased plasma levels. Uhlhaas, S., Lange, H. Brain Res. (1988) [Pubmed]
Pyroglutamic acid improves the age associated memory impairment. Grioli, S., Lomeo, C., Quattropani, M.C., Spignoli, G., Villardita, C. Fundamental & clinical pharmacology. (1990) [Pubmed]
Capillary electrophoresis for caffeine and pyroglutamate determination in coffees study of the in vivo effect on learning and locomotor activity in mice. Maeso, N., del Castillo, C., Cornejo, L., García-Acicollar, M., Alguacil, L.F., Barbas, C. Journal of pharmaceutical and biomedical analysis. (2006) [Pubmed]
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Crystal structures of human glutaminyl cyclase, an enzyme responsible for protein N-terminal pyroglutamate formation. Huang, K.F., Liu, Y.L., Cheng, W.J., Ko, T.P., Wang, A.H. Proc. Natl. Acad. Sci. U.S.A. (2005) [Pubmed]
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