ピロリドンカルボン酸
- 関
- magnesium pidolate、pyroglutamate、pyroglutamic acid
WordNet
- street name for lysergic acid diethylamide (同)back breaker, battery-acid, dose, dot, Elvis, loony toons, Lucy in the sky with diamonds, pane, superman, window pane, Zen
- any of various water-soluble compounds having a sour taste and capable of turning litmus red and reacting with a base to form a salt
- having the characteristics of an acid; "an acid reaction"
PrepTutorEJDIC
- 酸性の / 酸味のある,すっぱい(sour) / (言葉・態度などが)厳しい,しんらつな / 酸 / すっぱいもの / 《俗》=LSD
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/05/14 18:09:18」(JST)
[Wiki en表示]
Pyroglutamic acid
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| Names |
| Preferred IUPAC name
|
Systematic IUPAC name
5-Oxopyrrolidine-2-carboxylic acid
|
Other names
2-Pyrrolidone-5-carboxylic acid
Pidolic acid
5-Oxo-proline |
| Identifiers |
|
CAS Number
|
98-79-3 (2S) Y
4042-36-8 (2R) Y
149-87-1 Y |
| 3DMet |
B01549 |
| Abbreviations |
Glp |
|
Beilstein Reference
|
82134 |
| ChEBI |
CHEBI:16010 N |
| ChEMBL |
ChEMBL284718 N |
| ChemSpider |
7127 (2S) Y
388752 (2R) Y
485 Y
8710094 (2S)(3,4-3H2) Y |
| DrugBank |
DB03088 N |
| EC Number |
205-748-3 |
|
Gmelin Reference
|
1473408 |
|
IUPHAR/BPS
|
4703 |
| Jmol 3D model |
Interactive image |
| KEGG |
C02237 N |
| MeSH |
Pyrrolidonecarboxylic+acid |
| PubChem |
7405 (2S)
439685 (2R)
499
10534703 (2S)(3,4-3H2) |
| RTECS number |
TW3710000 |
| UNII |
SZB83O1W42 Y |
InChI
-
InChI=1S/C5H7NO3/c7-4-2-1-3(6-4)5(8)9/h3H,1-2H2,(H,6,7)(H,8,9) N
Key: ODHCTXKNWHHXJC-UHFFFAOYSA-N N
-
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
Key: ODHCTXKNWHHXJC-VKHMYHEASA-N
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|
|
| Properties |
|
Chemical formula
|
C5H7NO3 |
| Molar mass |
129.12 g·mol−1 |
| Melting point |
184 °C (363 °F; 457 K) |
| log P |
-0.89 |
| Acidity (pKa) |
-1.76, 3.48, 12.76 |
| Basicity (pKb) |
15.76, 10.52, 1.24 |
| Isoelectric point |
0.94 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|
| N verify (what is YN ?) |
| Infobox references |
|
|
Pyroglutamic acid (also known as PCA, 5-oxoproline, pidolic acid, or pyroglutamate for its basic form) is an uncommon and little studied amino acid derivative in which the free amino group of glutamic acid or glutamine cyclizes to form a lactam.[1] 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. 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]
Pyroglutamic acid, also known as pidolic acid, exists as two distinct enantiomers:
- (2R) or D which happens to be (+) or d
- (2S) or L which happens to be (–) or l
Metabolism
As first discovered in 1882, pyroglutamic acid can be formed by heating glutamic acid at 180 °C, which results in the loss of a molecule of water. In living cells, it is derived from glutathione through the action of an enzyme, γ-glutamyl cyclotransferase.[1] It may function to store glutamate, but also acts to oppose the action of glutamate including in the brain.[1] It also acts on the cholinergic system in the brain,[3] and Amyloid β containing pyroglutamic acid is increased in Alzheimer's disease and may be involved in the disease process.[4] Levels of pyroglutamic acid in the blood, called 5-oxoprolinuria, can increase following paracetamol overdose or in inborn error of metabolisms, causing an increased level of acidity called a high anion gap metabolic acidosis.[1][5]
Uses
The sodium salt of pyroglutamic acid – known either as sodium pyroglutamate, sodium PCA, or sodium pidolate – is used for dry skin and hair products, as it is a humectant. It has low toxicity and is not a skin irritant, but its use in products is limited by a high price.[6][7]
L-pyroglutamic acid is sold online as a dietary supplement.[8][9]
Magnesium pidolate, the magnesium salt of pyroglutamic acid, is a mineral supplement.
References
- ^ a b c d Kumar, Akhilesh; Bachhawat, Anand K. (January 25, 2012). "Pyroglutamic acid: throwing light on a lightly studied metabolite" (PDF) 102 (2): 208.
- ^ Podell, David N.; Abraham, George N. (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:10.1016/0006-291X(78)91646-7, PMID 26343 .
- ^ Pepeu, Giancarlo; Spignoli, Giacomo (1989). "Nootropic drugs and brain cholinergic mechanisms". Prog Neuropsychopharmacol Biol Psychiatry 13 (Supplement 1): S77–88.
- ^ Jawhar, S; Wirths, O; Bayer, TA (November 11, 2011). "Pyroglutamate amyloid-β (Aβ): a hatchet man in Alzheimer disease". J Biol Chem 286 (45): 38825–32. doi:10.1074/jbc.R111.288308.
- ^ Liss, DB; Paden, MS; Schwarz, ES; Mullins, ME (November 2013). "What is the clinical significance of 5-oxoproline (pyroglutamic acid) in high anion gap metabolic acidosis following paracetamol (acetaminophen) exposure?". Clin Toxicol (Phila). 51 (9): 817–27. doi:10.3109/15563650.2013.844822.
- ^ "Hydromol® (Alliance)". British National Formulary. Retrieved December 5, 2015.
- ^ Eric Jungermann, Norman O.V. Sonnta (eds.). "Alternatives to Glycerine". Glycerine: A Key Cosmetic Ingredient. p. 424.
- ^ DellaVecchia, Matthew J. (December 2013). "Inaccurate Serelaxin Chemical Structure". Pharmacy and Therapeutics 38 (12): 763.
- ^ McDougall, Jr., Graham J.; Austin-Wells, Vonnette; Zimmerman, Teena (December 2005). "Utility of Nutraceutical Products Marketed for Cognitive and Memory Enhancement". J Holist Nurs. 23 (4): 415–433. doi:10.1177/0898010105280097. (table 1)
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Protein primary structure and posttranslational modifications
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|
| General |
- Peptide bond
- Protein biosynthesis
- Proteolysis
- Racemization
- N-O acyl shift
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|
| N terminus |
- Acetylation
- Carbamylation
- Formylation
- Glycation
- Methylation
- Myristoylation (Gly)
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| C terminus |
- Amidation
- Glycosyl phosphatidylinositol (GPI)
- O-methylation
- Detyrosination
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| Single specific AAs |
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Serine/Threonine
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- Phosphorylation
- Dephosphorylation
- Glycosylation
- Methylidene-imidazolone (MIO) formation
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Tyrosine
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- Phosphorylation
- Dephosphorylation
- Sulfation
- Porphyrin ring linkage
- Adenylylation
- Flavin linkage
- Topaquinone (TPQ) formation
- Detyrosination
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Cysteine
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- Palmitoylation
- Prenylation
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Aspartate
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Glutamate
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- Carboxylation
- Methylation
- Polyglutamylation
- Polyglycylation
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Asparagine
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- Deamidation
- Glycosylation
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Glutamine
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Lysine
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- Methylation
- Acetylation
- Acylation
- Adenylylation
- Hydroxylation
- Ubiquitination
- Sumoylation
- ADP-ribosylation
- Deamination
- Oxidative deamination to aldehyde
- O-glycosylation
- Imine formation
- Glycation
- Carbamylation
- Succinylation
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Arginine
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- Citrullination
- Methylation
- ADP-ribosylation
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Proline
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Histidine
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- Diphthamide formation
- Adenylylation
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Tryptophan
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| Crosslinks between two AAs |
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Cysteine-Cysteine
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Methionine-Hydroxylysine
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Lysine-Tyrosylquinone
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- Lysine tyrosylquinone (LTQ) formation
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Tryptophan-Tryptophylquinone
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- Tryptophan tryptophylquinone (TTQ) formation
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Three consecutive AAs
(chromophore formation) |
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Serine–Tyrosine–Glycine
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- p-Hydroxybenzylidene-imidazolinone formation
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Histidine–Tyrosine–Glycine
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- 4-(p-hydroxybenzylidene)-5-imidazolinone formation
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| Crosslinks between four AAs |
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Allysine-Allysine-Allysine-Lysine
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UpToDate Contents
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English Journal
- Functional characterization of 5-oxoproline transport via SLC16A1/MCT1.
- Sasaki S1, Futagi Y1, Kobayashi M1, Ogura J1, Iseki K2.
- The Journal of biological chemistry.J Biol Chem.2015 Jan 23;290(4):2303-11. doi: 10.1074/jbc.M114.581892. Epub 2014 Nov 4.
- Thyrotropin-releasing hormone is a tripeptide that consists of 5-oxoproline, histidine, and proline. The peptide is rapidly metabolized by various enzymes. 5-Oxoproline is produced by enzymatic hydrolysis in a variety of peptides. Previous studies showed that 5-oxoproline could become a possible bio
- PMID 25371203
- Specificity studies on Kallikrein-related peptidase 7 (KLK7) and effects of osmolytes and glycosaminoglycans on its peptidase activity.
- Oliveira JR1, Bertolin TC1, Andrade D1, Oliveira LC1, Kondo MY1, Santos JA2, Blaber M3, Juliano L1, Severino B4, Caliendo G4, Santagada V4, Juliano MA5.
- Biochimica et biophysica acta.Biochim Biophys Acta.2015 Jan;1854(1):73-83. doi: 10.1016/j.bbapap.2014.10.018. Epub 2014 Oct 30.
- KLK7 substrate specificity was evaluated by families of fluorescence resonance energy transfer (FRET) peptides derived from Abz-KLFSSK-Q-EDDnp (Abz=ortho-aminobenzoic acid and Q-EDDnp=glutaminyl-N-[2,4-dinitrophenyl] ethylenediamine), by one bead-one peptide FRET peptide library in PEGA resin, and b
- PMID 25448018
- Molecular characterization, tissue distribution, and ultrastructural localization of adipokinetic hormones in the CNS of the firebug Pyrrhocoris apterus (Heteroptera, Insecta).
- Kodrík D1, Stašková T2, Jedličková V3, Weyda F4, Závodská R5, Pflegerová J2.
- General and comparative endocrinology.Gen Comp Endocrinol.2015 Jan 1;210:1-11. doi: 10.1016/j.ygcen.2014.10.014. Epub 2014 Oct 31.
- Adipokinetic hormones (AKHs) are a group of insect metabolic neurohormones, synthesized and released from an endocrine retrocerebral gland, the corpus cardiacum (CC). Small amounts of AKH have also been identified in the brain, although their role in this organ is not clear. To address this gap in t
- PMID 25449136
Japanese Journal
- イオン排除クロマトグラフィーによるL-グルタミンの精製法の研究
- Ring opening of pyrrolidonecarboxylic acid via a metal chelate.
- Effect of Several Penetration Enhancers on the Percutaneous Absorption of Indomethacin in Hairless Rats
Related Links
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★リンクテーブル★
[★]
ピドロ酸マグネシウム
- 関
- pyroglutamate、pyroglutamic acid、pyrrolidonecarboxylic acid
[★]
- 英
- pyrrolidonecarboxylic acid
- 関
- ピログルタミン酸、ピドロ酸マグネシウム