ピログルタミン酸
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)』「2014/08/26 16:36:07」(JST)
[Wiki en表示]
Pyroglutamic acid |
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Systematic name
5-Oxopyrrolidine-2-carboxylic acid
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Other names
Pidolic acid
5-Oxo-proline
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Identifiers |
Abbreviations |
Glp |
CAS number |
98-79-3 (2S) Y, 4042-36-8 (2R), 149-87-1 N |
PubChem |
7405 (2S), 439685 (2R), 499, 10534703 (2S)(3,4-3H2) |
ChemSpider |
7127 (2S) Y, 388752 (2R) Y, 485 Y, 8710094 (2S)(3,4-3H2) Y |
UNII |
SZB83O1W42 Y |
EC number |
205-748-3 |
DrugBank |
DB03088 |
KEGG |
C02237 N |
MeSH |
Pyrrolidonecarboxylic+acid |
ChEBI |
CHEBI:16010 N |
ChEMBL |
CHEMBL284718 N |
RTECS number |
TW3710000 |
Beilstein Reference |
82134 |
Gmelin Reference |
1473408 |
3DMet |
B01549 |
Jmol-3D images |
Image 1 |
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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 |
Molecular formula |
C5H7NO3 |
Molar mass |
129.11 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 noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa) |
N (verify) (what is: Y/N?) |
Infobox references |
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Pyroglutamic acid (also known as PCA, 5-oxoproline, pidolic acid, or pyroglutamate for its basic form) is an uncommon amino acid derivative in which the free amino group of glutamic acid or glutamine cyclizes to form a lactam. 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.[1]
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
Uses
The sodium salt of pyroglutamic acid – known either as sodium pyroglutamate or sodium pidolate – is used on the skin to retain moisture.[citation needed]
Pyroglutamic acid is sold as a dietary supplement in the United States.[citation needed]
References
- ^ 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 .
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 |
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
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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 |
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) |
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 |
Allysine-Allysine-Allysine-Lysine
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←Amino acids
Secondary structure→
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UpToDate Contents
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English Journal
- Unique mechanistic insights into the beneficial effects of angiotensin-(1-7) on the prevention of cardiac fibrosis: A metabolomic analysis of primary cardiac fibroblasts.
- Chen YL, Fan J, Cao L, Han TL, Zeng M, Xu Y, Ling Z, Yin Y.
- Experimental cell research. 2019 May;378(2)158-170.
- Cell metabolic pathways are highly conserved among species and change rapidly in response to drug stimulation. Therefore, we explore the effects of angiotensin-(1-7) in a primary cell model of cardiac fibrosis established in angiotensin II-stimulated cardiac fibroblasts via metabolomics analysis and
- PMID 30844388
- A metabolomics comparison between sheep's and goat's milk.
- Caboni P, Murgia A, Porcu A, Manis C, Ibba I, Contu M, Scano P.
- Food research international (Ottawa, Ont.). 2019 May;119()869-875.
- Despite the worldwide consumption of bovine milk, dairy products from small ruminants, such as goat's and sheep's milk, are gaining a large interest especially in the Mediterranean area. The aim of this work was to study the metabolite profiles of 30 sheep's and 28 goat's milk using an untargeted me
- PMID 30884727
- Metabolomics of Children and Adolescents Exposed to Industrial Carcinogenic Pollutants.
- Chen CS, Kuo TC, Kuo HC, Tseng YJ, Kuo CH, Yuan TH, Chan CC.
- Environmental science & technology. 2019 Apr;().
- Studies on metabolomes of carcinogenic pollutants among children and adolescents are limited. We aim to identify metabolic perturbations in 107 children and adolescents (aged 9-15) exposed to multiple carcinogens in a polluted area surrounding the largest petrochemical complex in Taiwan. We measured
- PMID 30971086
Japanese Journal
- Isolation and Identification of the Umami Enhancing Compounds in Japanese Soy Sauce
- KANEKO Shu,KUMAZAWA Kenji,NISHIMURA Osamu
- Bioscience, biotechnology, and biochemistry 75(7), 1275-1282, 2011-07-23
- … Liquid chromatography-time of flight mass spectrometry (LC-TOFMS), 1D/2D nuclear magnetic resonance spectroscopy (NMR) studies of the umami enhancing fractions led to the identification of <I>N</I>-(1-deoxy-D-fructos-1-yl)pyroglutamic acid (Fru-pGlu), <I>N</I>-(1-deoxy-D-fructos-1-yl)valine (Fru-Val), <I>N</I>-(1-deoxy-D-fructos-1-yl)methionine (Fru-Met), pyroglutamylglutamine (pGlu-Gln), and pyroglutamylglycine (pGlu-Gly). …
- NAID 10029329006
- 不飽和オルトピログルタミン酸エステルを用いる非タンパク性アミノ酸の立体選択的合成
- 大場 真
- 東海大学紀要. 開発工学部 20, 31-40, 2011-03-31
- 不飽和ピログルタミノール誘導体は天然物など光学活性化合物の合成中間体として広く用いられており,その有用性が認められているが合成上の問題から大量合成は困難とされている.本研究では不飽和ピログルタミン酸ABO エステルを新規なキラルテンプレートとして設計し,その合成に成功した.ABO 基は,α位のラセミ化を防ぐだけではなく酸加水分解によって容易にカルボキシル基を再生できる上,その立体的な嵩高さによって …
- NAID 110008146950
- Click Peptide : In Situ Production of pyroGlu-Abeta from the O-Acyl Isopeptide
- YAMASAKI Moe,SOHMA Youhei,TANIGUCHI Atsuhiko,HIRAYAMA Yuta,FURUYA Miki,MUKAI Hidehito,KISO Yoshiaki
- Peptide science : proceedings of the ... Japanese Peptide Symposium 2010, 210, 2011-03-01
- NAID 10028237887
Related Links
- ウィキペディアの英語版でPyroglutamic acidという用語が挙げてありますが、そこでは、以下の意味で使われています。Pyroglutamic acid (also known as PCA, 5-oxoproline, pidolic acid, or pyroglutamate for its basic form) is an uncommon amino acid ...
- Pyroglutamic Acid, You Can Buy Various High Quality Pyroglutamic Acid Products from Global Pyroglutamic Acid Suppliers and Pyroglutamic Acid Manufacturers at Alibaba.com Welcome Buy How to buy Post Buying Requests ...
★リンクテーブル★
[★]
- 英
- pyroglutamic acid、pyroglutamate
- 関
- ピドロ酸マグネシウム、ピロリドンカルボン酸
概念
- wikip jaより
その他
- サプリメントが存在する。効果の真偽については不明。
- Lピログルタミン酸 1000mg 120錠 2,256 円
記憶力や思考力、アルコールによる脳内ダメージのサポートに
脳の働きをアクティブにサポートするアミノ酸サプリメント「Lピログルタミン酸 1000mg」。記憶力や思考力アップを目指す方の脳内サポートはもちろん、スッキリした気分を引きだすストレスケアにも支持されています。
Lピログルタミン酸は、PCAとも呼ばれているアミノ酸の一種。私たちの脳や血液の中に多く存在しています。特に、脳の中でさまざまな情報を運んでいるアセチルコリンやGABAと深いかかわりがあるため、集中力や思考力を高める働きに期待がよせられています。また近年は、アルコールによる、記憶や脳のダメージのケアに注目を集めています。
本品は1粒に1000mgのLピログルタミン酸を配合。毎日の脳内サポートにオススメのサプリメントです。
参考
- http://www.chemicalbook.com.cn/CAS%5CGIF%5C98-79-3.gif
- http://ja.wikipedia.org/wiki/%E3%83%94%E3%83%AD%E3%82%B0%E3%83%AB%E3%82%BF%E3%83%9F%E3%83%B3%E9%85%B8
- http://www.sapoo.com/l-pyroglutamic-acid-1000mg-120-12680
[★]
ピドロ酸マグネシウム
- 関
- pyroglutamate、pyroglutamic acid、pyrrolidonecarboxylic acid
[★]
ピロリドンカルボン酸
- 関
- magnesium pidolate、pyroglutamate、pyroglutamic acid
[★]
ピログルタミン酸尿症