L-Norvaline
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L-Norvaline

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Category
L-Amino Acids
Catalog number
BAT-005596
CAS number
6600-40-4
Molecular Formula
C5H11NO2
Molecular Weight
117.10
L-Norvaline
IUPAC Name
(2S)-2-aminopentanoic acid
Synonyms
L-Nva-OH; L-2-Aminovaleric acid; (S)-2-Aminopentanoic acid
Appearance
White flakes.
Purity
≥ 99%
Density
1.067g/cm3
Melting Point
>300 °C
Boiling Point
228ºC
Storage
Store at RT
Solubility
water, 1.00E+05 mg/L @ 18C (exp)
InChI
InChI=1S/C5H11NO2/c1-2-3-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)/t4-/m0/s1
InChI Key
SNDPXSYFESPGGJ-BYPYZUCNSA-N
Canonical SMILES
CCCC(C(=O)O)N
1.Treatment effect of l-Norvaline on the sexual performance of male rats with streptozotocin induced diabetes.
De A1, Singh MF2, Singh V3, Ram V4, Bisht S4. Eur J Pharmacol. 2016 Jan 15;771:247-54. doi: 10.1016/j.ejphar.2015.12.008. Epub 2015 Dec 6.
Sexual impairment is an established risk factor in diabetes mellitus affecting about 75% of male diabetic population. In diabetes overexpression of arginase leads to decreased production of NO and diminished erectile response. Inhibition of arginase enzyme can lead to improvement in diabetes induced sexual dysfunction. In the present study diabetes mellitus was induced in adult male rats by intraperitoneal injection of single dose of streptozotocin (65mg/kg) in 0.1M Citrate buffer pH 4.5 and after 72h fasting serum glucose level was checked by glucose oxidase-peroxidase method and those animals showing FSG above 250mg/dl were selected. Diabetic animals were divided into four groups comprising six animals in each. l-Norvaline, potent arginase inhibitor was administered at a dose of 10mg/kg ip to the different groups of diabetic animals for a period of 30 days. Sildenafil at a dose of 5mg/kg orally was used as a standard drug. Mating behavior tests were performed at 0, 15th and 30th days.
2.New hydrophobic L-amino acid salts: maleates of L-leucine, L-isoleucine and L-norvaline.
Arkhipov SG1, Rychkov DA1, Pugachev AM2, Boldyreva EV1. Acta Crystallogr C Struct Chem. 2015 Jul;71(Pt 7):584-92. doi: 10.1107/S2053229615010888. Epub 2015 Jun 18.
Crystals of maleates of three amino acids with hydrophobic side chains [L-leucenium hydrogen maleate, C6H14NO2(+)·C4H3O4(-), (I), L-isoleucenium hydrogen maleate hemihydrate, C6H14NO2(+)·C4H3O4(-)·0.5H2O, (II), and L-norvalinium hydrogen maleate-L-norvaline (1/1), C5H11NO2(+)·C4H3O4(-)·C5H12NO2, (III)], were obtained. The new structures contain C2(2)(12) chains, or variants thereof, that are a common feature in the crystal structures of amino acid maleates. The L-leucenium salt is remarkable due to a large number of symmetrically non-equivalent units (Z' = 3). The L-isoleucenium salt is a hydrate despite the fact that L-isoleucine is a nonpolar hydrophobic amino acid (previously known amino acid maleates formed hydrates only with lysine and histidine, which are polar and hydrophilic). The L-norvalinium salt provides the first example where the dimeric cation L-Nva...L-NvaH(+) was observed. All three compounds have layered noncentrosymmetric structures.
3.Crystal structure of the tripeptide N-(benzyl-oxycarbon-yl)glycylglycyl-l-norvaline.
Nicholas S1. Acta Crystallogr E Crystallogr Commun. 2015 Feb 28;71(Pt 3):o216-7. doi: 10.1107/S205698901500393X. eCollection 2015.
The title tripeptide, C17H23N3O6, contains a nonproteinogenic C-terminal amino acid residue, norvaline, which is an isomer of the amino acid valine. Norvaline, unlike valine, has an unbranched side chain. The mol-ecule has a Gly-Gly segment which adopts an extended conformation. The norvaline residue also adopts an extended backbone conformation while its side chain has a g (+) t conformation. In the crystal lattice, N-H⋯O and O-H⋯O hydrogen bonds stabilize the packing. Mol-ecules translated along the crystallographic a axis associate through an N-H⋯O hydrogen bond. The remaining three hydrogen bonds are between mol-ecules related by a 2 1 screw axis.
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