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Revision as of 12:11, 6 December 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 463617556 of page Pyroglutamic_acid for the Chem/Drugbox validation project (updated: 'DrugBank', 'ChEMBL', 'ChEBI', 'KEGG', 'StdInChI', 'StdInChI...  Latest revision as of 12:06, 12 April 2024 edit M97uzivatel (talk | contribs)Extended confirmed users6,558 edits multispace 
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
{{Chembox {{Chembox
| Verifiedfields = changed | Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 458285726
| verifiedrevid = 464377606
| ImageFile = (S)-Pyroglutamic acid Structural Formulae.png
| ImageFile = Pyroglutamic acid.svg
| ImageName = Stereo structural formula of (2''S'')-pyroglutamic acid
| ImageSize = 140px
| PIN = Pidolic acid
| PIN = 5-Oxoproline
| SystematicName = 5-Oxopyrrolidine-2-carboxylic acid | SystematicName = 5-Oxopyrrolidine-2-carboxylic acid
| OtherNames = 5-Oxoproline<br /> | OtherNames = {{ubl|2-Pyrrolidone-5-carboxylic acid| Pidolic acid |5-Oxo-proline}}
5-Oxo-proline
| Section1 = {{Chembox Identifiers | Section1 = {{Chembox Identifiers
| Abbreviations = Glp | IUPHAR_ligand = 4703
| Abbreviations = Glp
| InChI = 1S/C5H7NO3/c7-4-2-1-3(6-4)5(8)9/h3H,1-2H2,(H,6,7)(H,8,9)/t3-/m0/s1
| InChI = 1S/C5H7NO3/c7-4-2-1-3(6-4)5(8)9/h3H,1-2H2,(H,6,7)(H,8,9)/t3-/m0/s1
| InChIKey1 = ODHCTXKNWHHXJC-VKHMYHEASA-N | InChIKey1 = ODHCTXKNWHHXJC-VKHMYHEASA-N
| InChI1 = 1S/C5H7NO3/c7-4-2-1-3(6-4)5(8)9/h3H,1-2H2,(H,6,7)(H,8,9)/t3-/m0/s1 | InChI1 = 1S/C5H7NO3/c7-4-2-1-3(6-4)5(8)9/h3H,1-2H2,(H,6,7)(H,8,9)/t3-/m0/s1
| CASNo2 = 149-87-1 | CASNo = 149-87-1
| CASNo_Comment = (''R/S'')
| CASNo2_Ref = {{cascite|changed|??}}
| CASNo_Ref = {{cascite|correct|??}}
| CASNo1 = 4042-36-8
| CASNo1_Ref = {{cascite|correct|??}}
| CASNo1_Comment = (2''R'')
| CASNo1 = 4042-36-8
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo1_Comment = (''R'')
| CASNo = 98-79-3
| CASNo2_Ref = {{cascite|correct|CAS}}
| CASNo_Comment = (2''S'')
| CASNo2 = 98-79-3
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo2_Comment = (''S'')
| PubChem2 = 499
| PubChem = 499
| PubChem2_Ref = {{Pubchemcite|correct|PubChem}}
| PubChem_Comment = (''R/S'')
| PubChem1 = 439685
| PubChem1_Comment = (2''R'') | PubChem1 = 439685
| PubChem1_Comment = (''R'')
| PubChem2 = 7405
| PubChem1_Ref = {{Pubchemcite|correct|PubChem}}
| PubChem2_Comment = (''S'')
| PubChem = 7405
| ChemSpiderID2 = 7127
| PubChem_Comment = (2''S'')
| ChemSpiderID2_Comment = (''S'')
| PubChem_Ref = {{Pubchemcite|correct|PubChem}}
| ChemSpiderID2_Ref = {{chemspidercite|correct|chemspider}}
| PubChem3 = 10534703
| ChemSpiderID1 = 388752
| PubChem3_Comment = (2''S'')(3,4-<sup>3</sup>''H''<sub>2</sub>)
| ChemSpiderID1_Comment = (''R'')
| PubChem3_Ref = {{Pubchemcite|correct|PubChem}}
| ChemSpiderID1_Ref = {{chemspidercite|correct|ChemSpider}}
| ChemSpiderID = 7127
| ChemSpiderID = 485
| ChemSpiderID_Comment = (2''S'')
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|ChemSpider}}
| ChemSpiderID_Comment = (''R/S'')
| ChemSpiderID1 = 388752
| UNII2_Ref = {{fdacite|correct|FDA}}
| ChemSpiderID1_Comment = (2''R'')
| UNII2 = SZB83O1W42
| ChemSpiderID1_Ref = {{Chemspidercite|correct|ChemSpider}}
| UNII2_Comment = (''S'')
| ChemSpiderID2 = 485
| UNII = 6VT1YZM21H
| ChemSpiderID2_Ref = {{Chemspidercite|correct|ChemSpider}}
| UNII_Ref = {{fdacite|correct|FDA}}
| ChemSpiderID3 = 8710094
| UNII_Comment = (''R/S'')
| ChemSpiderID3_Comment = (2''S'')(3,4-<sup>3</sup>''H''<sub>2</sub>)
| EINECS = 205-748-3
| ChemSpiderID3_Ref = {{Chemspidercite|correct|ChemSpider}}
| DrugBank_Ref = {{drugbankcite|changed|drugbank}}
| UNII = SZB83O1W42
| DrugBank = DB03088
| UNII_Ref = {{fdacite|correct|FDA}}
| KEGG_Ref = {{keggcite|changed|kegg}}
| EINECS = 205-748-3
| KEGG = C02237
| DrugBank_Ref = {{drugbankcite|changed|drugbank}}
| MeSHName = Pyrrolidonecarboxylic+acid
| DrugBank = <!-- blanked - oldvalue: DB03088 -->
| KEGG_Ref = {{keggcite|changed|kegg}} | ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 16010
| KEGG = <!-- blanked - oldvalue: C02237 -->
| ChEBI_Comment = (''R/S'')
| MeSHName = Pyrrolidonecarboxylic+acid
| ChEBI1 = 16924
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI1_Comment = (''R'')
| ChEBI = 18183
| RTECS = TW3710000 | ChEBI2 = 18183
| ChEBI2_Comment = (''S'')
| SMILES = O=C(O)1NC(=O)CC1
| RTECS = TW3710000
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| SMILES = O=C(O)1NC(=O)CC1
| ChEMBL = 397976
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 284718
| StdInChI_Ref = {{stdinchicite|changed|chemspider}} | StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C5H7NO3/c7-4-2-1-3(6-4)5(8)9/h3H,1-2H2,(H,6,7)(H,8,9)/t3-/m0/s1 | StdInChI = 1S/C5H7NO3/c7-4-2-1-3(6-4)5(8)9/h3H,1-2H2,(H,6,7)(H,8,9)
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = ODHCTXKNWHHXJC-VKHMYHEASA-N | StdInChIKey = ODHCTXKNWHHXJC-UHFFFAOYSA-N
| Gmelin = 1473408 | Gmelin = 1473408
| Beilstein = 82134 | Beilstein = 82134
| 3DMet = B01549}} | 3DMet = B01555
}}
| Section2 = {{Chembox Properties | Section2 = {{Chembox Properties
| C = 5 | C=5 | H=7 | N=1 | O=3
| H = 7 | MeltingPtC = 184
| N = 1 | LogP = -0.89
| O = 3 | pKa = -1.76, 3.48, 12.76
| pKb = 15.76, 10.52, 1.24
| ExactMass = 129.042593095 g mol<sup>-1</sup>
| MeltingPtC = 184 | IsoelectricPt = 0.94}}
|Section9={{Chembox Related
| LogP = -0.89
| OtherCompounds = ]<br/>]}}
| pKa = -1.76, 3.48, 12.76
| pKb = 15.76, 10.52, 1.24
| IsoelectricPt = 0.94}}
}} }}

'''Pyroglutamic acid''' (also known as '''PCA''', '''5-oxoproline''', '''pidolic acid''') is a ubiquitous but understudied natural ] derivative in which the free amino group of ] or ] ] to form a ].<ref name=throwing/> The names of pyroglutamic acid ], ], ]s, and ]s are '''pyroglutamate''', 5-oxoprolinate, or pidolate.
]
It is a metabolite in the glutathione cycle that is converted to glutamate by ]. Pyroglutamate is found in many proteins including ]. ] glutamic acid and glutamine residues can spontaneously cyclize to become pyroglutamate, or enzymatically converted by ].<ref>{{cite journal |last1=Schilling |first1=Stephan |last2=Wasternack |first2=Claus |last3=Demuth |first3=Hans-Ulrich |title=Glutaminyl cyclases from animals and plants: a case of functionally convergent protein evolution |journal=Biological Chemistry |date=1 August 2008 |volume=389 |issue=8 |pages=983–91 |doi=10.1515/BC.2008.111 |pmid=18979624 |s2cid=24074284}}</ref> This is one of several forms of blocked ''N''-termini which present a problem for ''N''-terminal sequencing using ], which requires a free primary amino group not present in pyroglutamic acid. The enzyme ] can restore a free ''N''-terminus by cleaving off the pyroglutamate residue.<ref>{{cite journal |last1=Podell |first1=David N. |last2=Abraham |first2=George N. |title=A technique for the removal of pyroglutamic acid from the amino terminus of proteins using calf liver pyroglutamate amino peptidase |journal=Biochemical and Biophysical Research Communications |date=March 1978 |volume=81 |issue=1 |pages=176–185 |doi=10.1016/0006-291X(78)91646-7 |pmid=26343}}</ref>

Pyroglutamic acid exists as two distinct ]:
*(2''R'') or <small>D</small> which happens to be (+) or ''d''
*(2''S'') or <small>L</small> which happens to be (–) or ''l''

==Metabolism==
As first discovered in 1882, pyroglutamic acid can be formed by heating glutamic acid at 180&nbsp;°C, which results in the loss of a molecule of water. In living cells, it is derived from ] through the action of an enzyme, ].<ref name=throwing/> Pyroglutamic acid may function in glutamate storage, and acts to oppose the action of glutamate, including in the brain.<ref name=throwing/> It also acts on the brain's ];<ref>{{cite journal |last1=Pepeu |first1=Giancarlo |last2=Spignoli |first2=Giacomo |title=Nootropic drugs and brain cholinergic mechanisms |journal=Progress in Neuro-Psychopharmacology and Biological Psychiatry |date=January 1989 |volume=13 |pages=S77–S88 |doi=10.1016/0278-5846(89)90112-7 |pmid=2694231 |s2cid=11309268 }}</ref> ] containing pyroglutamic acid is increased in ]; this may be part of the disease process.<ref>{{cite journal |last1=Jawhar |first1=Sadim |last2=Wirths |first2=Oliver |last3=Bayer |first3=Thomas A. |title=Pyroglutamate Amyloid-β (Aβ): A Hatchet Man in Alzheimer Disease |journal=Journal of Biological Chemistry |date=11 November 2011 |volume=286 |issue=45 |pages=38825–38832 |doi=10.1074/jbc.R111.288308 |pmid=21965666 |pmc=3234707 |doi-access=free}}</ref>
Increased levels of pyroglutamic acid in the blood, leading to excess in the urine (]), can occur following ], as well as in certain ], causing ].<ref name=throwing>{{cite journal |last1=Kumar |first1=Akhilesh |last2=Bachhawat |first2=Anand K. |title=Pyroglutamic acid: throwing light on a lightly studied metabolite |journal=Current Science |date=2012 |volume=102 |issue=2 |pages=288–297 |jstor=24083854 |url=http://www.currentscience.ac.in/Volumes/102/02/0288.pdf}}</ref><ref>{{cite journal |last1=Liss |first1=D. B. |last2=Paden |first2=M. S. |last3=Schwarz |first3=E. S. |last4=Mullins |first4=M. E. |title=What is the clinical significance of 5-oxoproline (pyroglutamic acid) in high anion gap metabolic acidosis following paracetamol (acetaminophen) exposure? |journal=Clinical Toxicology |date=11 October 2013 |volume=51 |issue=9 |pages=817–827 |doi=10.3109/15563650.2013.844822 |pmid=24111553 |s2cid=43541851}}</ref>

==Uses==
The ] ] of pyroglutamic acid—known either as sodium pyroglutamate, sodium PCA, or sodium pidolate—is used for ] and hair products, as it is a ]. It has low toxicity and is not a skin irritant, but its use in products is limited by a high price.<ref>{{cite web|url=https://www.evidence.nhs.uk/formulary/bnf/current/13-skin/132-emollient-and-barrier-preparations/1321-emollients/proprietary-emollient-preparations/hydromol|title=Hydromol® (Alliance)|work=British National Formulary|access-date=December 5, 2015}}</ref><ref>{{cite book|chapter-url=https://books.google.com/books?id=kGTsPEMNLt0C&pg=RA1-PA424|title=Glycerine: A Key Cosmetic Ingredient|chapter=Alternatives to Glycerine|editor1=Eric Jungermann |editor2=Norman O.V. Sonnta|page=424|isbn=978-0-8247-8465-2|last1=Jungermann|first1=Eric|last2=Sonntag|first2=Norman O.V|date=1991-07-19|publisher=CRC Press }}</ref>

<small>L</small>-pyroglutamic acid is sold online as a ] ].<ref>{{cite journal |last1=DellaVecchia |first1=Matthew J. |title=Inaccurate Serelaxin Chemical Structure |journal=Pharmacy and Therapeutics |date=December 2013 |volume=38 |issue=12 |pages=763 |pmid=24391398 |pmc=3875272 }}</ref><ref>{{cite journal |last1=McDougall |first1=Graham J. |last2=Austin-Wells |first2=Vonnette |last3=Zimmerman |first3=Teena |title=Utility of Nutraceutical Products Marketed for Cognitive and Memory Enhancement |journal=Journal of Holistic Nursing |date=24 June 2016 |volume=23 |issue=4 |pages=415–433 |doi=10.1177/0898010105280097 |pmid=16251490 |pmc=2398696 }}</ref>

], the magnesium salt of pyroglutamic acid, is found in some ]s.
In a preclinical study, additional pharmacological properties of pyroglutamic acid were revealed such as anti-], anti-], and anti-] activities.<ref>{{cite journal |last1=Šudomová |first1=Miroslava |last2=Hassan |first2=Sherif T. S. |last3=Khan |first3=Haroon |last4=Rasekhian |first4=Mahsa |last5=Nabavi |first5=Seyed Mohammad |title=A Multi-Biochemical and In Silico Study on Anti-Enzymatic Actions of Pyroglutamic Acid against PDE-5, ACE, and Urease Using Various Analytical Techniques: Unexplored Pharmacological Properties and Cytotoxicity Evaluation |journal=Biomolecules |date=21 August 2019 |volume=9 |issue=9 |pages=392 |doi=10.3390/biom9090392 |pmid=31438631 |pmc=6770154 |doi-access=free}}</ref>

==References==
{{reflist}}

{{Protein primary structure}}

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