Structure via PubChem · Public domain (PubChem)
L-norvaline
Sign in to saveAlso known as 2-Aminovaleric acid, L-2-aminopentanoic acid, L-2-Aminovaleric acid, (S)-2-Aminopentanoic acid, 2-Aminopentanoic acid, Norvaline
Norvaline (abbreviated as Nva) is an amino acid with the formula CH3(CH2)2CH(NH2)CO2H. The compound is a structural analog of valeric acid and also 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.
Chemical data
- Formula
- C5H11NO2
- Molecular weight
- 117.15 g/mol
- IUPAC name
- (2S)-2-aminopentanoic acid
- SMILES
- CCC[C@@H](C(=O)O)N
- InChIKey
- SNDPXSYFESPGGJ-BYPYZUCNSA-N
- XLogP
- -2.1
- Polar surface area
- 63.3 Ų
- H-bond donors
- 2
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Has part
- carbon
- Mass
- 117.079
Show 5 more facts
- canonical SMILES
- CCCC(C(=O)O)N
- chemical formula
- C₅H₁₁NO₂
- isomeric SMILES
- CCC[C@@H](C(=O)O)N
- found in taxon
- Serratia marcescens
- Commons category
- Norvaline
via Wikidata · CC0
~2 min read
Encyclopedic overview
4 sectionsContents
- Occurrence
- Nomenclature
- Potential uses
- References
Norvaline (abbreviated as Nva) is an amino acid with the formula CH3(CH2)2CH(NH2)CO2H. The compound is a structural analog of valeric acid and also 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.
==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. 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.
Excerpted from Wikipedia’s “L-norvaline” article, available under the CC BY-SA 4.0 licence.