L-バリン
- 関
- valine
WordNet
- the 12th letter of the Roman alphabet (同)l
- an essential amino acid found in proteins; important for growth in children and nitrogen balance in adults
PrepTutorEJDIC
- lira(イタリアの貨幣単位リラ)
- liter[s]
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/11/24 08:55:51」(JST)
[Wiki en表示]
Valine
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| Names |
| IUPAC name
Valine
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| Other names
2-amino-3-methylbutanoic acid
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| Identifiers |
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CAS Number
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516-06-3 Y
72-18-4 (L-isomer) Y
640-68-6 (D-isomer) Y |
| ChEBI |
CHEBI:57762 Y |
| ChEMBL |
ChEMBL43068 Y |
| ChemSpider |
6050 Y |
| DrugBank |
DB00161 Y |
| EC Number |
208-220-0 |
InChI
-
InChI=1S/C5H11NO2/c1-3(2)4(6)5(7)8/h3-4H,6H2,1-2H3,(H,7,8)/t4-/m0/s1 Y
Key: KZSNJWFQEVHDMF-BYPYZUCNSA-N Y
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InChI=1/C5H11NO2/c1-3(2)4(6)5(7)8/h3-4H,6H2,1-2H3,(H,7,8)/t4-/m0/s1
Key: KZSNJWFQEVHDMF-BYPYZUCNBW
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IUPHAR/BPS
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4794 |
| Jmol interactive 3D |
Image |
| KEGG |
D00039 Y |
| PubChem |
1182 |
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| UNII |
4CA13A832H Y |
| Properties[2] |
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Chemical formula
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C5H11NO2 |
| Molar mass |
117.15 g·mol−1 |
| Density |
1.316 g/cm3 |
| Melting point |
298 °C (568 °F; 571 K) (decomposition) |
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Solubility in water
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soluble |
| Acidity (pKa) |
2.32 (carboxyl), 9.62 (amino)[1] |
| Supplementary data page |
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Structure and
properties
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Refractive index (n),
Dielectric constant (εr), etc. |
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Thermodynamic
data
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Phase behaviour
solid–liquid–gas |
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Spectral data
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UV, IR, NMR, MS |
| Y verify (what is YN ?) |
| Infobox references |
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Valine (abbreviated as Val or V)[3] is an essential, proteinogenic α-amino acid with the chemical formula HO2CCH(NH2)CH(CH3)2. Val is classified as nonpolar. Its codons are GUU, GUC, GUA, and GUG. Human dietary sources are any proteinaceous foods such as meats, dairy products, soy products, beans and legumes.
Along with leucine and isoleucine, valine is a branched-chain amino acid. It is named after the plant valerian. In sickle-cell disease, valine substitutes for the hydrophilic amino acid glutamic acid in β-globin. Because valine is hydrophobic, the hemoglobin is prone to abnormal aggregation.
Contents
- 1 Nomenclature
- 2 Biosynthesis
- 3 Synthesis
- 4 References
- 5 See also
- 6 External links
Nomenclature
According to IUPAC, carbon atoms forming valine are numbered sequentially starting from 1 denoting the carboxyl carbon, whereas 4 and 4' denote the two terminal methyl carbons.[4]
Biosynthesis
Valine is an essential amino acid, hence it must be ingested, usually as a component of proteins. It is synthesized in plants via several steps starting from pyruvic acid. The initial part of the pathway also leads to leucine. The intermediate α-ketoisovalerate undergoes reductive amination with glutamate. Enzymes involved in this biosynthesis include:[5]
- Acetolactate synthase (also known as acetohydroxy acid synthase)
- Acetohydroxy acid isomeroreductase
- Dihydroxyacid dehydratase
- Valine aminotransferase
Synthesis
Racemic valine can be synthesized by bromination of isovaleric acid followed by amination of the α-bromo derivative[6]
- HO2CCH2CH(CH3)2 + Br2 → HO2CCHBrCH(CH3)2 + HBr
- HO2CCHBrCH(CH3)2 + 2 NH3 → HO2CCH(NH2)CH(CH3)2 + NH4Br
References
- ^ Dawson, R.M.C., et al., Data for Biochemical Research, Oxford, Clarendon Press, 1959.
- ^ Weast, Robert C., ed. (1981). CRC Handbook of Chemistry and Physics (62nd ed.). Boca Raton, FL: CRC Press. p. C-569. ISBN 0-8493-0462-8.
- ^ "Nomenclature and symbolism for amino acids and peptides (IUPAC-IUB Recommendations 1983)", Pure Appl. Chem. 56 (5), 1984: 595–624, doi:10.1351/pac198456050595 .
- ^ Jones, J. H., ed. (1985). Amino Acids, Peptides and Proteins. Specialist Periodical Reports 16. London: Royal Society of Chemistry. p. 389. ISBN 978-0-85186-144-9.
- ^ Lehninger, Albert L.; Nelson, David L.; Cox, Michael M. (2000), Principles of Biochemistry (3rd ed.), New York: W. H. Freeman, ISBN 1-57259-153-6 .
- ^ Marvel, C. S. (1940). "dl-Valine". Org. Synth. 20: 106. ; Coll. Vol. 3, p. 848 .
See also
External links
- Valine MS Spectrum
- Isoleucine and valine biosynthesis
- Valine's relationship to prions
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The encoded amino acid
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| General topics |
- Protein
- Peptide
- Genetic code
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| By properties |
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Aliphatic
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- Branched-chain amino acids (Valine
- Isoleucine
- Leucine)
- Methionine
- Alanine
- Proline
- Glycine
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Aromatic
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- Phenylalanine
- Tyrosine
- Tryptophan
- Histidine
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Polar, uncharged
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- Asparagine
- Glutamine
- Serine
- Threonine
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Positive charge (pKa)
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- Lysine (≈10.8)
- Arginine (≈12.5)
- Histidine (≈6.1)
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Negative charge (pKa)
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- Aspartic acid (≈3.9)
- Glutamic acid (≈4.1)
- Cysteine (≈8.3)
- Tyrosine (≈10.1)
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| Other classifications |
- Essential amino acid
- Ketogenic amino acid
- Glucogenic amino acid
- Non-proteinogenic amino acid
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Index of biochemical families
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| Carbohydrates |
- Alcohols
- Glycoproteins
- Glycosides
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| Lipids |
- Eicosanoids
- Fatty acids
- Glycerides
- Phospholipids
- Sphingolipids
- Steroids
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| Nucleic acids |
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| Proteins |
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| Other |
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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-Ketoadipate
- 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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- Agmatine
- Ornithine
- Cadaverine
- Putrescine
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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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Index of inborn errors of metabolism
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| Description |
- Metabolism
- Enzymes and pathways: citric acid cycle
- pentose phosphate
- glycoproteins
- glycosaminoglycans
- phospholipid
- cholesterol and steroid
- sphingolipids
- eicosanoids
- amino acid
- urea cycle
- nucleotide
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| Disorders |
- Citric acid cycle and electron transport chain
- Glycoprotein
- Proteoglycan
- Fatty-acid
- Phospholipid
- Cholesterol and steroid
- Eicosanoid
- Amino acid
- Purine-pyrimidine
- Heme metabolism
- Symptoms and signs
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| Treatment |
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Index of biochemical families
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| Carbohydrates |
- Alcohols
- Glycoproteins
- Glycosides
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| Lipids |
- Eicosanoids
- Fatty acids
- Glycerides
- Phospholipids
- Sphingolipids
- Steroids
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| Nucleic acids |
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| Proteins |
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| Other |
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UpToDate Contents
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English Journal
- The role of various amino acids in enzymatic browning process in potato tubers, and identifying the browning products.
- Ali HM1, El-Gizawy AM2, El-Bassiouny RE3, Saleh MA3.
- Food chemistry.Food Chem.2016 Feb 1;192:879-85. doi: 10.1016/j.foodchem.2015.07.100. Epub 2015 Jul 23.
- The effects of five structurally variant amino acids, glycine, valine, methionine, phenylalanine and cysteine were examined as inhibitors and/or stimulators of fresh-cut potato browning. The first four amino acids showed conflict effects; high concentrations (⩾100mM for glycine and ⩾1.0M for the
- PMID 26304424
- Metabolomics and microbiological profile of Italian mozzarella cheese produced with buffalo and cow milk.
- Pisano MB1, Scano P2, Murgia A3, Cosentino S1, Caboni P4.
- Food chemistry.Food Chem.2016 Feb 1;192:618-24. doi: 10.1016/j.foodchem.2015.07.061. Epub 2015 Jul 16.
- Italian buffalo mozzarella (BM) cheese metabolite profile and microbial communities were characterised and compared to cow mozzarella (CM). Polar metabolite profiles were studied by gas-chromatography mass-spectrometry (GC-MS) and results elaborated by multivariate analysis (MVA). BM produced using
- PMID 26304391
- Interaction of bovine serum albumin with N-acyl amino acid based anionic surfactants: Effect of head-group hydrophobicity.
- Ghosh S1, Dey J2.
- Journal of colloid and interface science.J Colloid Interface Sci.2015 Nov 15;458:284-92. doi: 10.1016/j.jcis.2015.07.064. Epub 2015 Jul 29.
- The function of a protein depends upon its structure and surfactant molecules are known to alter protein structure. For this reason protein-surfactant interaction is important in biological, pharmaceutical, and cosmetic industries. In the present work, interactions of a series of anionic surfactants
- PMID 26245717
Japanese Journal
- Serum Metabolomics in Rats after Acute Paraquat Poisoning
- Synthesis and Anti-microbial Activity of Novel Phosphatidylethanolamine-N-amino Acid Derivatives
- Synthesis and Anti-microbial Activity of Novel Phosphatidylethanolamine-N-amino Acid Derivatives
Related Pictures
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- L-valine、V、Val