(2R)-2-amino-3-methylbutanoic acid

• ChemBase ID: 102837
• Molecular Formular: C5H11NO2
• Molecular Mass: 117.14634
• Monoisotopic Mass: 117.0789786
• SMILES: CC(C)[C@@H](N)C(=O)O
• Canonical SMILES: N[C@@H](C(=O)O)C(C)C
• InChI: InChI=1S/C5H11NO2/c1-3(2)4(6)5(7)8/h3-4H,6H2,1-2H3,(H,7,8)/t4-/m1/s1
• InChIKey: KZSNJWFQEVHDMF-SCSAIBSYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-amino-3-methylbutanoic acid
• IUPAC Traditional name: D-valine
• Synonyms: D-2-Amino-3-methylbutanoic acid; D-α-Aminoisovaleric acid; D-VALINE; D-Valine; (R)-α-Aminoisovaleric acid; D-2-Aminoisovaleric acid; (R)-(-)-2-Amino-3-methylbutyric acid; (2R)-2-amino-3-methylbutanoic acid; (-)-2-Amino-3-methylbutyric Acid; (R)-3-Methyl-2-aminobutanoic Acid; (R)-Valine; D-(-)-Valine; NSC 20654; D-α-氨基异戊酸; D-2-氨基-3-甲基丁酸; D-缬氨酸

Database IDs

• CAS Number: 640-68-6
• EC Number: 211-368-9
• MDL Number: MFCD00064219
• Beilstein Number: 1721135
• PubChem SID: 162088293; 24890031; 24900713; 24888396
• PubChem CID: 71563

CALCULATED PROPERTIES

• Acid pKa: 2.7172735
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -1.9534721
• LogD (pH = 7.4): -1.9554411
• Log P: -1.9531364
• Molar Refractivity: 29.4929 cm^3
• Polarizability: 12.004493 Å^3
• Polar Surface Area: 63.32 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: > 285°C; >295 °C (subl.)(lit.); 295°C dec.
• Optical Rotation: [α]20/D -27.0±0.5°, c = 5% in 5 M HCl; [α]23/D -32.0 to -24.0°, c = 8 in 6 M HCl; -27 (c=5 in 5N HCl)
• Hydrophobicity(logP): -2.286

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• RTECS: YV9360000
• German water hazard class: 3
• TSCA Listed: 是
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥98%; ≥99.0% (NT); 95%; 98+%; 99%
• Grade: puriss.
• Optical Purity: ee: 99% (GLC)
• Suitability: suitable for cell culture
• Linear Formula: (CH3)2CHCH(NH2)CO2H

DETAILS

MP Biomedicals - 02103226

Crystalline
Purity: 99%

Sigma Aldrich - V1255

Application
D-valine is used in cell culture as a selective inhibitor of cell proliferation, wherein it inhibits cells that lack the enzyme D-amino acid oxidase. Historically D-valine has been used to inhibit fibroblast growth while allowing selective growth of epithelial cells.
General description
L-Valine is an essential non-polar amino acid. D-Valine is the non-proteinogenic isomer of valine.

Sigma Aldrich - 855987

Packaging
25 g in poly bottle
5 g in glass bottle

Toronto Research Chemicals - V094200

D-Valine is an isomer of the essential amino acid L-Valine. D-Valine has been used as a selective agent in epithelial cells in culture since it inhibits cells that lack the enzyme D-amino acid oxidase. D-Valine has also been shown to inhibit proliferation

REFERENCES

• Gilbert, S.F. et al.: Cell, 5, 11 (1975)
• Hongpaisan, J. et al.: Cell Biol. Int., 24, 1 (1975)
• Sasamura, T. et al.: J, Nutrit. Sci. Vitaminol., 44, 89 (1975)