Norvaline

Names

IUPAC name

2-Aminopentanoic acid

Other names

2-Aminovaleric acid; α-Aminopentanoic acid; Propylglycine

Identifiers

CAS Number

6600-40-4

3D model (JSmol)

ChEMBL

ChEMBL55612

ChemSpider

58608 (L)
801 (DL)
388660 (D)

ECHA InfoCard

100.026.858

PubChem CID

65098

InChI

(L): InChI=1S/C5H11NO2/c1-2-3-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)/t4-/m0/s1

Key: SNDPXSYFESPGGJ-BYPYZUCNSA-N
(DL): InChI=1S/C5H11NO2/c1-2-3-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)

Key: SNDPXSYFESPGGJ-UHFFFAOYSA-N
(D): InChI=1S/C5H11NO2/c1-2-3-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)/t4-/m1/s1

Key: SNDPXSYFESPGGJ-SCSAIBSYSA-N

SMILES

(L): CCC[C@@H](C(=O)O)N
(DL): CCCC(C(=O)O)N
(D): CCC[C@H](C(=O)O)N

Properties

Chemical formula

C₅H₁₁NO₂

Molar mass

117.15 g·mol⁻¹

Acidity (pK_a)

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).

(what is ^YN ?)

Infobox references

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.

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 is known to promote tissue regeneration and muscle growth, and to become a precursor in the penicillin biosynthetic pathway.

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.

...
Wikipedia