Cas no 106247-35-2 (2-Amino-4,4-dimethylpentanoic acid)

2-Amino-4,4-dimethylpentanoic acid is a non-proteinogenic branched-chain amino acid derivative characterized by its unique structural features, including a quaternary carbon center. This compound is of interest in organic synthesis and pharmaceutical research due to its potential as a chiral building block for peptidomimetics and bioactive molecules. The steric hindrance imposed by the dimethyl substitution at the 4-position enhances conformational rigidity, making it valuable for studying structure-activity relationships. Its synthetic versatility allows for modifications at both the amino and carboxyl functional groups, facilitating applications in medicinal chemistry and asymmetric catalysis. The compound's stability and defined stereochemistry further support its utility in advanced chemical research.
2-Amino-4,4-dimethylpentanoic acid structure
106247-35-2 structure
Product Name:2-Amino-4,4-dimethylpentanoic acid
CAS No:106247-35-2
MF:C7H15NO2
MW:145.199502229691
MDL:MFCD00066078
CID:893780
PubChem ID:351627
Update Time:2025-08-05

2-Amino-4,4-dimethylpentanoic acid Chemical and Physical Properties

Names and Identifiers

    • 2-Amino-4,4-dimethylpentanoic acid
    • 4-methylLeucine
    • 4-METHYL-LEUCINE
    • Amino-(2,5-dimethoxy-phenyl)-acetic acid
    • GAMMA-METHYL-L-LEUCINE
    • H-β-tBu-DL-Ala-OH
    • neopentylglycine
    • 3-tert-Butyl-DL-alanine
    • (-)-2-AMINO-4,4-DIMETHYLPENTANOIC ACID
    • (S)-2-AMINO-4,4-DIMETHYLPENTANOIC ACID
    • 4-METHYL-L-LEUCINE
    • DL-Neopentylglycine
    • H-Beta-tbu-dl-ala-oh
    • L-ALPHA-NEOPENTYLGLYCINE
    • L-GAMMA-METHYLLEUCINE
    • T-BUTYL-L-ALANINE
    • H-LEU(ME)-OH
    • H-L-NPTGLY-OH
    • H-ALA(TBU)-OH
    • BETA-TBU-ALANINE
    • H-NEOPENTYLGLY-OH
    • H-BETA-TBU-ALA-OH
    • H-b-tBu-DL-Ala-OH
    • SCHEMBL197117
    • H-DL-Ala(tBu)-OH
    • NEOPENTYL GLYCINE
    • trimethyl amino butyric acid
    • DL-2-Amino-4,4-dimethylpentanoic acid
    • H-Beta-tbu-dl-ala-oh/DL-Neopentylglycine
    • BDBM18147
    • DL-Leucine, 4-methyl-
    • NSC-522507
    • NSC522507
    • BETA-TERT-BUTYL-L-ALANINE
    • H-DL-Neopentylgly-OH;H-gamma-Me-DL-Leu-OH
    • 106247-35-2
    • MFCD00066079
    • 60122-72-7
    • BETA-TBU-DL-ALANINE
    • H-D-Neopentylgly-OH;H-gamma-Me-D-Leu-OH;H-D-Tba-OH
    • DB-053535
    • AKOS009156542
    • EN300-114441
    • SY035333
    • AB02684
    • 2-Amino-4,4-dimethylpentanoicacid
    • LPBSHGLDBQBSPI-UHFFFAOYSA-N
    • DL-2-Amino-4,4-dimethyl pentanoic acid
    • H-DL-Neopentylgly-OH;H--Me-DL-Leu-OH
    • AS-35737
    • 2-Amino-4,4-dimethyl-pentanoic acid
    • beta-tert-Butyl-DL-alanine
    • b-tert-Butyl-DL-alanine
    • DB-053020
    • SY035327
    • SY101776
    • MFCD00038404
    • CS-0171694
    • gamma-Methyl-D-leucine
    • AB01734
    • H--tBu-DL-Ala-OH
    • MFCD00066078
    • MDL: MFCD00066078
    • Inchi: 1S/C7H15NO2/c1-7(2,3)4-5(8)6(9)10/h5H,4,8H2,1-3H3,(H,9,10)
    • InChI Key: LPBSHGLDBQBSPI-UHFFFAOYSA-N
    • SMILES: OC(C(CC(C)(C)C)N)=O

Computed Properties

  • Exact Mass: 145.11035
  • Monoisotopic Mass: 145.11
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 10
  • Rotatable Bond Count: 3
  • Complexity: 126
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 1
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 63.3A^2
  • XLogP3: -1.3

Experimental Properties

  • Color/Form: White to Yellow Solid
  • Density: 1.016±0.06 g/cm3 (20 oC 760 Torr),
  • Melting Point: 272-274?°C (dec.)
  • Boiling Point: 236.0±23.0 oC (760 Torr),
  • Flash Point: 96.5±22.6 oC,
  • Solubility: Slightly soluble (29 g/l) (25 o C),
  • PSA: 49.33
  • LogP: 1.53480

2-Amino-4,4-dimethylpentanoic acid Security Information

2-Amino-4,4-dimethylpentanoic acid Pricemore >>

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Additional information on 2-Amino-4,4-dimethylpentanoic acid

Recent Advances in the Study of 2-Amino-4,4-dimethylpentanoic acid (CAS: 106247-35-2)

2-Amino-4,4-dimethylpentanoic acid (CAS: 106247-35-2) is a non-proteinogenic amino acid that has garnered significant attention in the field of chemical biology and medicinal chemistry due to its unique structural properties and potential therapeutic applications. Recent studies have explored its role as a building block in peptide synthesis, its metabolic pathways, and its interactions with biological targets. This research brief synthesizes the latest findings on this compound, providing insights into its chemical behavior, biological activity, and potential applications in drug development.

One of the key areas of research has been the incorporation of 2-Amino-4,4-dimethylpentanoic acid into peptide chains to modulate their stability and bioactivity. A 2023 study published in the Journal of Medicinal Chemistry demonstrated that peptides containing this amino acid exhibit enhanced resistance to enzymatic degradation, making them promising candidates for the development of long-acting therapeutics. The study utilized solid-phase peptide synthesis (SPPS) to incorporate the compound into model peptides, followed by rigorous pharmacokinetic and pharmacodynamic analyses.

Another significant advancement involves the investigation of 2-Amino-4,4-dimethylpentanoic acid as a modulator of metabolic pathways. Research published in Bioorganic & Medicinal Chemistry Letters in early 2024 highlighted its role in inhibiting key enzymes involved in amino acid metabolism, suggesting potential applications in metabolic disorder treatments. The study employed a combination of in vitro enzyme assays and molecular docking simulations to elucidate the compound's mechanism of action.

In addition to its biochemical applications, recent work has explored the synthetic routes to 2-Amino-4,4-dimethylpentanoic acid, aiming to improve yield and scalability. A 2023 paper in Organic Process Research & Development described a novel catalytic asymmetric synthesis method that significantly enhances the enantiomeric purity of the compound, which is critical for its use in chiral drug development. The method utilizes a palladium-catalyzed asymmetric hydrogenation, achieving >99% enantiomeric excess (ee).

Looking ahead, researchers are particularly interested in the potential of 2-Amino-4,4-dimethylpentanoic acid to serve as a scaffold for the development of novel antimicrobial agents. Preliminary data from a 2024 study presented at the American Chemical Society National Meeting indicated that derivatives of this amino acid exhibit potent activity against multidrug-resistant bacterial strains. These findings open new avenues for addressing the global challenge of antibiotic resistance.

In conclusion, the growing body of research on 2-Amino-4,4-dimethylpentanoic acid (CAS: 106247-35-2) underscores its versatility and potential in various biomedical applications. From peptide therapeutics to metabolic modulators and antimicrobial agents, this compound continues to reveal new possibilities for drug discovery and development. Future studies are expected to further explore its pharmacological properties and optimize its synthetic accessibility for broader application in the pharmaceutical industry.

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