ウロカニン酸
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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/09/01 15:05:35」(JST)
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| Urocanic acid |
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IUPAC name
(E)-3-(1H-imidazol-4-yl)prop-2-enoic acid
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| Identifiers |
| CAS number |
104-98-3 Y |
| PubChem |
1178 |
| MeSH |
Urocanic+acid |
| ChEBI |
CHEBI:30817 N |
| Jmol-3D images |
Image 1 |
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InChI=1S/C6H6N2O2/c9-6(10)2-1-5-3-7-4-8-5/h1-4H,(H,7,8)(H,9,10)/b2-1+ N
Key: LOIYMIARKYCTBW-OWOJBTEDSA-N N
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| Properties |
| Molecular formula |
C6H6N2O2 |
| Molar mass |
138.124 g/mol |
| Melting point |
225°C |
| 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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Urocanic acid is an intermediate in the catabolism of L-histidine.
Contents
- 1 Metabolism
- 2 Clinical significance
- 3 Function
- 4 History
- 5 See also
- 6 References
- 7 External links
Metabolism
It is formed from L-histidine through the action of histidine ammonialyase (also known as histidase or histidinase) by elimination of ammonium.
In the liver, urocanic acid is transformed by urocanate hydratase (or urocanase) to 4-imidazolone-5-propionic acid and subsequently to glutamic acid.
Clinical significance
Inherited deficiency of urocanase leads to elevated levels of urocanic acid in the urine, a condition known as urocanic aciduria.
Function
Urocanic acid was detected in animal sweat and skin where, among other possible functions, it acts as an endogenous sunscreen or photoprotectant against UVB-induced DNA damage. Urocanic acid is found predominantly in the stratum corneum of the skin and it is likely that most of it is derived from filaggrin catabolism (a histidine-rich protein). When exposed to UVB irradiation, trans-urocanic acid is converted in vitro and in vivo to the cis isomer.[1] The cis form is known to activate regulatory T cells.[2]
History
Urocanic acid was first isolated in 1874 by the chemist Max Jaffé from the urine of a dog,[3][4][5] hence the name (Latin: urina = urine, and canis = dog).
See also
- Histidinemia
- Inborn error of metabolism
References
- ^ Egawa M, Nomura J, Iwaki H: The evaluation of the amount of cis- and trans-urocanic acid in the stratum corneum by Raman spectroscopy. Photochem. Photobiol. Sci., 2010, 9, 730-733.
- ^ Schwarz T: Mechanisms of UV-induced immunosuppression. Keio J Med 2005;54(4):165-171.
- ^ Jaffé, M. (1874). "Concerning a new constituent in the urine of dogs". Ber. Deut. Chem. Ges. 7: 1669–1673.
- ^ M. Jaffe: Ueber die Urocaninsäure. In: Berichte der deutschen chemischen Gesellschaft. - Weinheim : Wiley-VCH, ISSN 0365-9496 Vol. 8 (1. 1875), p. 811-813.
- ^ M. Jaffe: Ueber einen neuen Bestandtheil des Hundeharns. In: Berichte der deutschen chemischen Gesellschaft. - Weinheim : Wiley-VCH, ISSN 0365-9496 Vol. 7 (2. 1874), p. 1669-1673.
External links
- The Online Metabolic and Molecular Bases of Inherited Disease - Chapter 80 - An overview of disorders of histidine metabolism, including urocanic aciduria.
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Amino acid metabolism metabolic intermediates
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| K→acetyl-CoA |
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lysine→
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- Saccharopine
- Allysine
- α-Aminoadipic acid
- α-Aminoadipate
- Glutaryl-CoA
- Glutaconyl-CoA
- Crotonyl-CoA
- β-Hydroxybutyryl-CoA
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leucine→
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- α-Ketoisocaproic acid
- Isovaleryl-CoA
- 3-Methylcrotonyl-CoA
- 3-Methylglutaconyl-CoA
- HMG-CoA
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tryptophan→alanine→
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- N'-Formylkynurenine
- Kynurenine
- Anthranilic acid
- 3-Hydroxykynurenine
- 3-Hydroxyanthranilic acid
- 2-Amino-3-carboxymuconic semialdehyde
- 2-Aminomuconic semialdehyde
- 2-Aminomuconic acid
- Glutaryl-CoA
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| G |
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G→pyruvate→citrate
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glycine→serine→
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- glycine→creatine: Glycocyamine
- Phosphocreatine
- Creatinine
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G→glutamate→
α-ketoglutarate
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histidine→
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- Urocanic acid
- Imidazol-4-one-5-propionic acid
- Formiminoglutamic acid
- Glutamate-1-semialdehyde
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proline→
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- 1-Pyrroline-5-carboxylic acid
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arginine→
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- Ornithine
- Putrescine
- Agmatine
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other
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- cysteine+glutamate→glutathione: γ-Glutamylcysteine
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G→propionyl-CoA→
succinyl-CoA
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valine→
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- α-Ketoisovaleric acid
- Isobutyryl-CoA
- Methacrylyl-CoA
- 3-Hydroxyisobutyryl-CoA
- 3-Hydroxyisobutyric acid
- 2-Methyl-3-oxopropanoic acid
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isoleucine→
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- 2,3-Dihydroxy-3-methylpentanoic acid
- 2-Methylbutyryl-CoA
- Tiglyl-CoA
- 2-Methylacetoacetyl-CoA
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methionine→
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- generation of homocysteine: S-Adenosyl methionine
- S-Adenosyl-L-homocysteine
- Homocysteine
- conversion to cysteine: Cystathionine
- alpha-Ketobutyric acid+Cysteine
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threonine→
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propionyl-CoA→
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G→fumarate
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phenylalanine→tyrosine→
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- 4-Hydroxyphenylpyruvic acid
- Homogentisic acid
- 4-Maleylacetoacetic acid
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G→oxaloacetate
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| Other |
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mt, k, c/g/r/p/y/i, f/h/s/l/o/e, a/u, n, m
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k, cgrp/y/i, f/h/s/l/o/e, au, n, m, epon
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m (A16/C10), i (k, c/g/r/p/y/i, f/h/s/o/e, a/u, n, m)
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- Biochemical families: carbohydrates
- alcohols
- glycoproteins
- glycosides
- lipids
- eicosanoids
- fatty acids / intermediates
- glycerides
- phospholipids
- sphingolipids
- steroids
- nucleic acids
- constituents / intermediates
- proteins
- Amino acids / intermediates
- tetrapyrroles / intermediates
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English Journal
- Radiation-Resistant Micrococcus luteus SC1204 and Its Proteomics Change Upon Gamma Irradiation.
- Deng W1,2, Yang Y1, Gao P3,4, Chen H3, Wen W1, Sun Q5.
- Current microbiology.Curr Microbiol.2016 Feb 26. [Epub ahead of print]
- To explore the radiation-resistance mechanisms in bacteria, a radiation-resistant strain SC1204 was isolated from the surrounding area of a 60Co-γ radiation facility. SC1204 could survive up to 8 kGy dose of gamma irradiation and was identified as Micrococcus luteus by phylogenetic analysis of 16S
- PMID 26920868
- Protective Effect of Chitin Urocanate Nanofibers against Ultraviolet Radiation.
- Ito I1, Yoneda T2, Omura Y3, Osaki T4, Ifuku S5, Saimoto H6, Azuma K7, Imagawa T8, Tsuka T9, Murahata Y10, Ito N11, Okamoto Y12, Minami S13.
- Marine drugs.Mar Drugs.2015 Dec 19;13(12):7463-75. doi: 10.3390/md13127076.
- Urocanic acid is a major ultraviolet (UV)-absorbing chromophore. Chitins are highly crystalline structures that are found predominantly in crustacean shells. Alpha-chitin consists of microfibers that contain nanofibrils embedded in a protein matrix. Acid hydrolysis is a common method used to prepare
- PMID 26703629
- Role of the Transporter-Like Sensor Kinase CbrA in Histidine Uptake and Signal Transduction.
- Zhang XX1, Gauntlett JC2, Oldenburg DG2, Cook GM3, Rainey PB4.
- Journal of bacteriology.J Bacteriol.2015 Sep;197(17):2867-78. doi: 10.1128/JB.00361-15. Epub 2015 Jul 6.
- CbrA is an atypical sensor kinase found in Pseudomonas. The autokinase domain is connected to a putative transporter of the sodium/solute symporter family (SSSF). CbrA functions together with its cognate response regulator, CbrB, and plays an important role in nutrient acquisition, including regulat
- PMID 26148710
Japanese Journal
- ウロカナーゼ反応の立体化学 : ウロカニン酸C-4'位のH-基交換について
- Effect of Diphenylhydantoin Administration on Single Carbon Metabolism in Folate Deficient Rats
- Narisawa Kuniaki [他],HONDA YOSHIYUKI,ARAKAWA TSUNEO
- The Tohoku Journal of Experimental Medicine 110(4), 359-365, 1973
- … When rats were made folate deficient and given diphenylhydantoin (DPH), it was found that there were an increase in formation of 14CO2 from urocanate-2-14C and histidine-2-14C by liver slices, a decrease in urinary formiminoglutamic acid (FIGLU) after urocanate load, and an increase in the incorporation of formate-14C into serine by liver slices. …
- NAID 130004821692
- Urocanic Aciduria: A Defect in the Urocanase Activity in the Liver of a Mentally Retarded
- YOSHIDA TOSHIO,TADA KEIYA,HONDA YOSHIYUKI,ARAKAWA TSUNEO
- The Tohoku Journal of Experimental Medicine 104(4), 305-312, 1971
- … This was characterized by 1) urocanic aciduria, which was exaggerated after an oral dose of L-histidine, 2) a delayed clearance curve of serum histidine levels after an oral dose of L-histidine, 3) urinary excretion of no detectable amounts of formiminoglutamic acid after an oral load with L-histidine or after an intravenous injection of urocanate, 4) a marked decrease in the urocanase activity of the liver, and 5) mental retardation of probably early onset. …
- NAID 130003491555
Related Links
- Urocanate definition at Dictionary.com, a free online dictionary with pronunciation, synonyms and translation. Look it up now! Thesaurus Translate Puzzles & Games Reference Word of the Day Blog Slideshows Apps by Dictionary ...
- How would you define urocanate? Add your definition here. Words near urocanate in the dictionary urobilinogen uroboric urocanase urocanases urocanate urocanates urocanic urocanic-acid urocele uroceles Top Rated Word Lists ...
Related Pictures
★リンクテーブル★
[★]
- 英
- urocanic acid, urocanate
- 同
- 4-イミダゾールアクリル酸 4-imidazoleacrylic acid
- 関
- ヒスチジン
[★]
ウロカニン酸ヒドラターゼ