{{chembox | Watchedfields = | verifiedrevid = 378432403 | Name = Norvaline | ImageFileL1 = D-Norvalin.svg | ImageFileR1 = L-Norvalin.svg | IUPACName=2-Aminopentanoic acid | OtherNames=2-Aminovaleric acid; α-Aminopentanoic acid; Propylglycine |Section1={{Chembox Identifiers | CASNo = 6600-40-4 | CASNo_Ref = {{cascite|correct|CAS}} | UNII_Ref = {{fdacite|correct|FDA}} | UNII = A70UKS48FE | ChemSpiderID = 58608 | ChemSpiderID_Comment = (<small>L</small>) | ChemSpiderID1 = 801 | ChemSpiderID1_Comment = (<small>DL</small>) | ChemSpiderID2 = 388660 | ChemSpiderID2_Comment = (<small>D</small>) | ChEMBL = 55612 | PubChem = 65098 | IUPHAR_ligand = | SMILES = CCC[C@@H](C(=O)O)N | SMILES_Comment = (<small>L</small>) | SMILES1 = CCCC(C(=O)O)N | SMILES1_Comment = (<small>DL</small>) | SMILES2 = CCC[C@H](C(=O)O)N | SMILES2_Comment = (<small>D</small>)
| InChI = 1S/C5H11NO2/c1-2-3-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)/t4-/m0/s1 | InChI_Comment = (<small>L</small>) | InChIKey = SNDPXSYFESPGGJ-BYPYZUCNSA-N
| InChI1 = 1S/C5H11NO2/c1-2-3-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8) | InChI1_Comment = (<small>DL</small>) | InChIKey1 = SNDPXSYFESPGGJ-UHFFFAOYSA-N
| InChI2 = 1S/C5H11NO2/c1-2-3-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)/t4-/m1/s1 | InChI2_Comment = (<small>D</small>) | InChIKey2 = SNDPXSYFESPGGJ-SCSAIBSYSA-N
}} |Section2={{Chembox Properties | C=5 | H=11 | N=1 | O=2 | Appearance = | Density = | MeltingPt = | BoilingPt = | pKa=2.36 (carboxyl), 9.76 (amino)<ref>Dawson, R.M.C., et al., ''Data for Biochemical Research'', Oxford, Clarendon Press, 1959.{{page needed|date=January 2015}}</ref> | Solubility = }} |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} }}
'''Norvaline''' (abbreviated as '''Nva''') is an amino acid with the formula CH<sub>3</sub>(CH<sub>2</sub>)<sub>2</sub>CH(NH<sub>2</sub>)CO<sub>2</sub>H. The compound is a structural analog of valeric acid and also an isomer of the more common amino acid valine.<ref>[http://www.merriam-webster.com/medical/norvaline Merriam-Webster] Retrieved 4 September 2010</ref> Like most other α-amino acids, norvaline is chiral. It is a white, water-soluble solid.
==Occurrence== 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''.<ref>{{cite journal |vauthors=Soini J, Falschlehner C, Liedert C, Bernhardt J, Vuoristo J, Neubauer P |title=Norvaline is accumulated after a down-shift of oxygen in Escherichia coli W3110 |journal=Microbial Cell Factories |volume=7 |article-number=30 |year=2008 |pmid=18940002 |pmc=2579280 |doi=10.1186/1475-2859-7-30 |doi-access=free }}</ref> 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.<ref>{{cite journal |vauthors=Alvarez-Carreño C, Becerra A, Lazcano A |title=Norvaline and norleucine may have been more abundant protein components during early stages of cell evolution |journal=Origins of Life and Evolution of the Biosphere |volume=43 |issue=4–5 |pages=363–75 | date=October 2013 |pmid=24013929 |doi=10.1007/s11084-013-9344-3|bibcode=2013OLEB...43..363A |s2cid=17224537 }}</ref>
==Nomenclature== 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, and the IUPAC/IUB Joint Commission on Nomenclature recommends that this name should be abandoned and the systematic name should be used.<ref>{{cite journal | title = Nomenclature and Symbolism For Amino Acids and Peptides | journal = Pure and Applied Chemistry | volume = 56 | issue = 5 | pages = 595–624 | date = 1984|doi=10.1351/pac198456050595 | doi-access = free }}</ref>
==Potential uses== Norvaline is used as a dietary supplement for bodybuilding. Recently, it was suggested in the treatment of Alzheimer's disease.<ref>Polis, B., Srikanth, K. D., Gurevich, V., Gil-Henn, H., & Samson, A. O. (2019). L-Norvaline, a new therapeutic agent against Alzheimer’s disease. Neural regeneration research, 14(9), 1562.</ref>
==References== {{reflist}}
{{Non-proteinogenic amino acids}}
Category:Alpha-Amino acids Category:Biochemistry Category:Non-proteinogenic amino acids