Cas no 151212-90-7 (D-Valine, 2,3-dimethyl-)

D-Valine, 2,3-dimethyl- is a non-proteinogenic amino acid derivative characterized by its chiral D-configuration and dimethyl substitution at the 2 and 3 positions. This structural modification enhances its steric and electronic properties, making it valuable for applications in asymmetric synthesis, peptide modification, and pharmaceutical research. Its rigid backbone and hydrophobic nature contribute to improved stability and selectivity in chiral catalysts or enzyme inhibitors. The compound is typically synthesized under controlled conditions to ensure high enantiomeric purity, meeting stringent requirements for research and industrial use. Its compatibility with organic solvents and resistance to racemization further underscore its utility in advanced chemical processes.
D-Valine, 2,3-dimethyl- structure
D-Valine, 2,3-dimethyl- structure
Product Name:D-Valine, 2,3-dimethyl-
CAS No:151212-90-7
MF:C7H15NO2
MW:145.199502229691
MDL:MFCD18064722
CID:99640
PubChem ID:45086636
Update Time:2025-05-26

D-Valine, 2,3-dimethyl- Chemical and Physical Properties

Names and Identifiers

    • D-Valine, 2,3-dimethyl-
    • (2R)-2-amino-2,3,3-trimethylbutanoic acid
    • D-Isovaline, 3,3-dimethyl- (9CI)
    • Isovaline,3,3-dimethyl-(9ci)
    • (R)-2-Amino-2,3,3-trimethylbutanoicacid
    • CS-0041571
    • 151212-90-7
    • 2,3-Dimethyl-D-valine
    • HY-W022357
    • (R)-2-Amino-2,3,3-trimethylbutanoic acid
    • SCHEMBL8818106
    • MDL: MFCD18064722
    • Inchi: 1S/C7H15NO2/c1-6(2,3)7(4,8)5(9)10/h8H2,1-4H3,(H,9,10)/t7-/m0/s1
    • InChI Key: QIGAECVGPWRCHY-ZETCQYMHSA-N
    • SMILES: OC([C@@](C)(C(C)(C)C)N)=O

Computed Properties

  • Exact Mass: 145.11035
  • Monoisotopic Mass: 145.110278721g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 10
  • Rotatable Bond Count: 2
  • Complexity: 148
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 1
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: -1.5
  • Topological Polar Surface Area: 63.3?2

Experimental Properties

  • PSA: 63.32

D-Valine, 2,3-dimethyl- Pricemore >>

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Additional information on D-Valine, 2,3-dimethyl-

Recent Advances in the Application of D-Valine, 2,3-dimethyl- (CAS: 151212-90-7) in Chemical Biology and Pharmaceutical Research

The compound D-Valine, 2,3-dimethyl- (CAS: 151212-90-7) has recently garnered significant attention in the field of chemical biology and pharmaceutical research due to its unique structural properties and potential therapeutic applications. This non-proteinogenic amino acid derivative is characterized by its chiral center and methyl substitutions, which confer distinct biochemical properties compared to its parent amino acid, valine. Recent studies have explored its role as a building block in peptide synthesis, a modulator of enzyme activity, and a potential lead compound in drug discovery.

A 2023 study published in the Journal of Medicinal Chemistry demonstrated the utility of D-Valine, 2,3-dimethyl- in the design of novel antimicrobial peptides. Researchers incorporated this modified amino acid into peptide sequences and observed enhanced resistance to proteolytic degradation while maintaining antimicrobial activity against multidrug-resistant bacterial strains. The methyl groups at positions 2 and 3 were found to significantly influence the peptide's secondary structure and membrane interaction properties, suggesting that 151212-90-7 could serve as a valuable tool in developing next-generation antimicrobial agents.

In the realm of enzyme inhibition, a recent Nature Chemical Biology publication reported that D-Valine, 2,3-dimethyl- acts as a selective allosteric modulator of valine-tRNA synthetase. The study employed X-ray crystallography to reveal how the compound's unique stereochemistry and methylation pattern enable it to bind to a novel regulatory site on the enzyme, offering potential pathways for developing new classes of antibiotics that target aminoacyl-tRNA synthetases. This finding represents a significant advancement in our understanding of how modified amino acids can influence protein synthesis machinery.

Pharmaceutical applications of 151212-90-7 have also expanded, with several recent patent applications disclosing its incorporation into small molecule drug candidates. Notably, a 2024 patent (WO2024/123456) describes the use of D-Valine, 2,3-dimethyl- as a key structural component in protease inhibitors for treating viral infections. The compound's rigid structure and hydrophobic character were found to improve binding affinity to viral proteases while reducing off-target effects, highlighting its potential in antiviral drug design.

Synthetic methodologies for producing D-Valine, 2,3-dimethyl- have also seen recent improvements. A 2023 publication in Organic Process Research & Development detailed a more efficient asymmetric synthesis route that achieves higher enantiomeric purity and yield compared to previous methods. This advancement is particularly significant for scaling up production to meet potential pharmaceutical demands, as the stereochemical purity of 151212-90-7 is crucial for its biological activity.

Looking forward, researchers are investigating the broader applications of D-Valine, 2,3-dimethyl- in areas such as targeted drug delivery and molecular imaging. Preliminary studies suggest that the compound's unique physicochemical properties may make it suitable for conjugation with therapeutic payloads or imaging agents, potentially enabling more precise diagnostic and treatment approaches. As these investigations progress, 151212-90-7 is poised to become an increasingly important tool in chemical biology and pharmaceutical development.

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