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N7502

Sigma-Aldrich

DL-Norvaline

≥98% (HPLC), suitable for HPLC

Synonym(s):

(±)-2-Aminopentanoic acid

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About This Item

Linear Formula:
CH3CH2CH2CH(NH2)COOH
CAS Number:
760-78-1
Molecular Weight:
117.15
Beilstein:
1721163
EC Number:
212-082-7
MDL number:
MFCD00064420
UNSPSC Code:
12352209
PubChem Substance ID:
24897829
NACRES:
NA.26

Product Name

DL-Norvaline,

Assay

≥98% (HPLC)

Quality Level

200

form

powder

technique(s)

HPLC: suitable

color

white

mp

>300 °C

SMILES string

CCCC(N)C(O)=O

InChI

1S/C5H11NO2/c1-2-3-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)

InChI key

SNDPXSYFESPGGJ-UHFFFAOYSA-N

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General description

Norvaline is a non-proteinogenic α-amino acid and is also called DL-α-aminovaleric acid. It is produced in Gram-negative microorganisms including Escherichia coli and is also a part of the antifungal peptide produced by Bacillus subtilis.

Application

DL-Norvaline has been used as an internal standard:
  • to analyze metabolites in cultured mammalian cells by gas chromatography-mass spectrometry (GC-MS)
  • to convert cysteine and cystine to Cys MPA (S-2-carboxyethylthio-L-cysteine) and quantify the same using a high-performance liquid chromatography (HPLC) analyzer
  • for free amino acid analysis in samples of oocytes by liquid chromatography

Biochem/physiol Actions

DL-Norvaline is a neurotransmitter.
Norvaline mediates physiological and pathophysiological processes promoting nitric oxide production. It is used to treat Alzheimer′s disease and is effective against artificial metabolic syndrome in rats. Norvaline exhibits phase transition upon cooling below 190 K and hence it is useful in molecular machines. DL-Norvaline serves as a prototype for research in polymorphism and molecular dynamics of aliphatic α-amino acids containing linear side-chain. It influences the activity, stability, and side-chain packaging of proteins.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

N7502-1G:
N7502-100G:
N7502-25G:
N7502-500G:
N7502-1KG:
N7502-BULK:
N7502-VAR:

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Certificates of Analysis (COA)

Lot/Batch Number
SLCG1151
SLBZ9874
SLBV2278
SLBP7955V
SLBC3242V

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Jens Neu et al.
Physical chemistry chemical physics : PCCP, 20(1), 276-283 (2017-12-06)
dl-Norvaline is a molecular crystal at room temperature and it undergoes a phase transition when cooled below 190 K. This phase transition is believed to be Martensitic, thus making it of particular interest for molecular machines. In this paper we
Esther W Lim et al.
Methods in molecular biology (Clifton, N.J.), 2088, 51-71 (2020-01-02)
Oxidation-reduction (redox) reactions are ubiquitous in biology and typically occur in specific subcellular compartments. In cells, the electron transfer between molecules and organelles is commonly facilitated by pyridine nucleotides such as nicotinamide adenine dinucleotide phosphate (NADPH) and nicotinamide adenine dinucleotide
W Sosroseno et al.
Oral microbiology and immunology, 21(3), 145-150 (2006-04-22)
The aim of the present study was to determine whether or not lipopolysaccharide from Actinobacillus actinomycetemcomitans could stimulate arginase activity in a murine macrophage cell line (RAW264.7 cells). RAW264.7 cells were treated with A. actinomycetemcomitans-lipopolysaccharide or lipopolysaccharide from Escherichia coli
Carl Henrik Görbitz
The journal of physical chemistry. B, 115(10), 2447-2453 (2011-02-22)
The amino acid DL-norvaline undergoes two solid-solid phase transitions between room temperature and -180 °C. Single-crystal X-ray diffraction studies show that the first of these transitions, taking place around -80 °C, is completely reversible with respect to crystal quality, whereas
Ramasamy Sankaranarayanan et al.
Journal of molecular biology, 375(4), 1052-1063 (2007-12-08)
Mycobacterium tuberculosis ornithine carbamoyltransferase (Mtb OTC) catalyzes the sixth step in arginine biosynthesis; it produces citrulline from carbamoyl phosphate (CP) and ornithine (ORN). Here, we report the crystal structures of Mtb OTC in orthorhombic (form I) and hexagonal (form II)
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Chromatograms

application for HPLC

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