Norvaline (abbreviated as Nva) is an amino acid with the formula CH3(CH2)2CH(NH2)CO2H. The compound is an isomer of the more common amino acid valine. Like most other α-amino acids, norvaline is chiral. It is a white, water-soluble solid.
2-Aminovaleric acid; α-Aminopentanoic acid; Propylglycine
3D model (JSmol)
|Molar mass||117.15 g·mol−1|
|Acidity (pKa)||2.36 (carboxyl), 9.76 (amino)|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Norvaline is a non-proteinogenic unbranched-chain amino acid. It has previously been reported to be a natural component of an antifungal peptide of Bacillus subtilis. Norvaline and other modified unbranched chain amino acids have received attention because they appear to be incorporated in some recombinant proteins found in E. coli. Its biosynthesis has been examined. The incorporation of Nva into peptides reflects the imperfect selectivity of the associated aminoacyl-tRNA synthetase. In Miller–Urey experiments probing prebiotic synthesis of amino acids, norvaline, but also norleucine, are produced.
Norvaline and norleucine (one hydrocarbon group longer) both possess the nor- prefix for historical reason, despite current conventional usage of the prefix to denote a missing hydrocarbon group (under which they would theoretically be called "dihomoalanine" and "trihomoalanine"). The name is not systematic.
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- Merriam-Webster Retrieved 4 September 2010
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- Ming XF, Rajapakse AG, Carvas JM, Ruffieux J, Yang Z (2009). "Inhibition of S6K1 accounts partially for the anti-inflammatory effects of the arginase inhibitor L-norvaline". BMC Cardiovascular Disorders. 9: 12. doi:10.1186/1471-2261-9-12. PMC 2664787. PMID 19284655.
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