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Valine |
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| Systematic (IUPAC) name | |
| (S)-2-amino-3-methyl-butanoic acid | |
| Identifiers | |
| CAS number | 72-18-4 |
| PubChem | 1182 |
| Chemical data | |
| Formula | C5H11NO2 |
| Molar mass | 117.15 g/mol |
| SMILES | CC(C)C(N)C(=O)O |
| Complete data | |
Valine (abbreviated as Val or V)[1] is an α-amino acid with the chemical formula HO2CCH(NH2)CH(CH3)2. L-Valine is one of 20 proteogenic amino acids. Its codons are GUU, GUC, GUA, and GUG. This essential amino acid is classified as nonpolar. 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 hemoglobin. Because valine is hydrophobic, the hemoglobin does not fold correctly.
Contents |
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-ketovalerate undergoes reductive amination with glutamate. Enzymes involved in this biosynthesis include:[2]
- 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[3]
- HO2CCH2CH(CH3)2 + Br2 → HO2CCHBrCH(CH3)2 + HBr
- HO2CCHBrCH(CH3)2 + 2 NH3 → HO2CCH(NH2)CH(CH3)2 + NH4Br
Dietary aspects
Nutritional sources of valine include cottage cheese, fish, poultry, peanuts, sesame seeds, and lentils.
References
- ^ IUPAC-IUBMB Joint Commission on Biochemical Nomenclature. "Nomenclature and Symbolism for Amino Acids and Peptides". Recommendations on Organic & Biochemical Nomenclature, Symbols & Terminology etc. Retrieved on 2007-05-17.
- ^ Nelson, D. L.; Cox, M. M. "Lehninger, Principles of Biochemistry" 3rd Ed. Worth Publishing: New York, 2000. ISNB 1-57259-153-6.
- ^ Marvel, C. S. “d,l-Valine” Organic Syntheses, Collected Volume 3, p.848 (1955). http://www.orgsyn.org/orgsyn/pdfs/CV3P0848.pdf
External links
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Wikipedia content modification information:
- This page was last modified on 24 September 2008, at 00:15.
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