Cas no 300583-35-1 ((2S)-2-amino-3-(tert-butylsulfanyl)propanoic acid)

(2S)-2-amino-3-(tert-butylsulfanyl)propanoic acid is a non-proteinogenic amino acid derivative featuring a tert-butylthio side chain. This compound is of interest in peptide chemistry and medicinal research due to its sterically hindered thioether functionality, which enhances stability against oxidative degradation. The chiral (S)-configuration at the α-carbon ensures compatibility with stereoselective synthesis. Its tert-butylsulfanyl group provides a hydrophobic moiety, useful for modulating peptide lipophilicity or probing steric effects in enzyme-substrate interactions. The compound serves as a versatile intermediate in the development of thioether-containing bioactive molecules, offering controlled reactivity for selective modifications. High purity grades are available for research applications requiring precise structural integrity.
(2S)-2-amino-3-(tert-butylsulfanyl)propanoic acid structure
300583-35-1 structure
Product Name:(2S)-2-amino-3-(tert-butylsulfanyl)propanoic acid
CAS No:300583-35-1
MF:C7H15NO2S
MW:177.2645008564
CID:304336
PubChem ID:6951060
Update Time:2025-10-31

(2S)-2-amino-3-(tert-butylsulfanyl)propanoic acid Chemical and Physical Properties

Names and Identifiers

    • D-Cysteine,S-(1,1-dimethylethyl)-
    • L-S-T-BUTYLCYSTEINE
    • L-S-TERT-BUTYLCYSTEINE
    • S-tert-Butyl-D-cysteine
    • (2S)-2-amino-3-(tert-butylsulfanyl)propanoic acid
    • (S)-2-Amino-3-(S-t-Butylthio)propanoic Acid
    • (S)-2-amino-3-(tert-butylthio)propanoic acid
    • (S)-tert-Butyl-D-Cys
    • 300583-35-1
    • D-S-tert-Butylcysteine
    • (2S)-2-amino-3-tert-butylsulfanylpropanoic acid
    • SCHEMBL622880
    • H-D-Cys(tBu)-OH
    • EN300-1720468
    • Inchi: 1S/C7H15NO2S/c1-7(2,3)11-4-5(8)6(9)10/h5H,4,8H2,1-3H3,(H,9,10)/t5-/m1/s1
    • InChI Key: VADVRIAPCDFQJU-RXMQYKEDSA-N
    • SMILES: S(C[C@H](C(=O)O)N)C(C)(C)C

Computed Properties

  • Exact Mass: 177.08200
  • Monoisotopic Mass: 177.08234989g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 11
  • Rotatable Bond Count: 4
  • Complexity: 142
  • 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: -1.7
  • Topological Polar Surface Area: 88.6?2

Experimental Properties

  • PSA: 88.62000
  • LogP: 1.63030

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Additional information on (2S)-2-amino-3-(tert-butylsulfanyl)propanoic acid

Introduction to CAS No. 300583-35-1: (2S)-2-amino-3-(tert-butylsulfanyl)propanoic Acid

CAS No. 300583-35-1, commonly referred to as (2S)-2-amino-3-(tert-butylsulfanyl)propanoic acid, is a compound of significant interest in the fields of organic chemistry and pharmacology. This compound is characterized by its unique stereochemistry and functional groups, which contribute to its diverse applications in drug discovery and chemical synthesis. The tert-butylsulfanyl group attached to the propanoic acid backbone adds a layer of complexity, making it a valuable molecule for exploring sulfur-containing compounds in biological systems.

Recent studies have highlighted the potential of (2S)-2-amino-3-(tert-butylsulfanyl)propanoic acid in modulating cellular signaling pathways, particularly those involving sulfur-containing biomolecules. Researchers have demonstrated that this compound exhibits selective binding properties towards certain enzymes, suggesting its role as a lead compound in the development of novel therapeutic agents. The amino group in its structure plays a critical role in its interaction with biological targets, further underscoring its importance in medicinal chemistry.

The synthesis of CAS No. 300583-35-1 involves a multi-step process that requires precise control over stereochemistry to ensure the correct configuration at the chiral center. Advanced techniques such as enantioselective catalysis and stereoselective oxidation have been employed to achieve high yields of the desired enantiomer. These methods not only enhance the efficiency of synthesis but also pave the way for large-scale production, making this compound more accessible for research and development purposes.

In terms of biological activity, (2S)-2-amino-3-(tert-butylsulfanyl)propanoic acid has shown promising results in preclinical studies targeting inflammatory diseases and neurodegenerative disorders. Its ability to inhibit key inflammatory mediators has positioned it as a potential candidate for anti-inflammatory therapies. Furthermore, ongoing research is exploring its role in modulating oxidative stress pathways, which could have implications for treating conditions associated with oxidative damage.

The structural features of this compound, including its tert-butylsulfanyl group and amino functionality, make it an ideal substrate for further chemical modifications. Scientists are actively investigating derivative compounds to expand its pharmacological profile and improve bioavailability. These efforts are supported by computational modeling techniques that predict the behavior of these derivatives in biological systems, enabling a more targeted approach to drug design.

From an analytical standpoint, the characterization of CAS No. 300583-35-1 has benefited from advancements in spectroscopic techniques such as NMR and mass spectrometry. These tools provide detailed insights into the compound's molecular structure and purity, ensuring high standards of quality control in both research and manufacturing settings.

In conclusion, (2S)-2-amino-3-(tert-butylsulfanyl)propanoic acid represents a compelling molecule with wide-ranging applications in chemistry and medicine. Its unique properties, coupled with ongoing research into its biological effects, position it as a key player in the development of innovative therapeutic solutions. As scientific understanding of this compound continues to grow, so too does its potential to contribute to advancements in healthcare and beyond.

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