Cas no 167479-78-9 (L-(S)-4-Cyanophenylalanine)

L-(S)-4-Cyanophenylalanine is a non-natural amino acid derivative featuring a cyano group at the para position of the phenyl ring. This modification enhances its utility in peptide synthesis and bioconjugation, particularly in the development of bioactive peptides and probes for structural studies. The cyano group serves as a versatile handle for further chemical modifications, enabling applications in click chemistry and fluorescence labeling. Its high purity and stereochemical integrity make it suitable for rigorous research in medicinal chemistry and enzymology. The compound’s stability and compatibility with standard solid-phase peptide synthesis protocols further underscore its value as a building block for advanced biochemical and pharmaceutical research.
L-(S)-4-Cyanophenylalanine structure
L-(S)-4-Cyanophenylalanine structure
Product Name:L-(S)-4-Cyanophenylalanine
CAS No:167479-78-9
MF:C10H10N2O2
MW:190.198602199554
MDL:MFCD00270363
CID:65778
PubChem ID:1501865
Update Time:2025-06-08

L-(S)-4-Cyanophenylalanine Chemical and Physical Properties

Names and Identifiers

    • (S)-2-Amino-3-(4-cyanophenyl)propanoic acid
    • L-4-Cyanophe
    • H-Phe(4-CN)-OH
    • 4-Cyano-L-Phenylalanine
    • H-4-Cyano-Phe-OH
    • L-4-Cyanophenylalanine
    • (L)-4-Cyanophenylalanine
    • L-(S)-4-Cyanophenylalanine
    • (2S)-2-Amino-3-(4-cyanophenyl)propanoic acid
    • L-PHE(4-CN)
    • (P-CN)PHE-OH
    • L-4-CN-Phe-OH
    • H-PHE(P-CN)-OH
    • H-p-Cyano-Phe-OH
    • L-4-Cyano-phe-OH
    • H-P-CYANO-L-PHE-OH
    • 4-Cyanophenylalanine
    • Phenylalanine, 4-cyano-
    • (s)-2-amino-3-(4-cyanophenyl)propionic acid
    • L-4- Cyanophenylalanine
    • p-cyanophenylalanine
    • DL-4-Cyanophenylalanine
    • L-4-Cyano phenylalanine
    • para-Cyano-L-phenylalanine
    • 167479-78-9
    • KWIPUXXIFQQMKN-VIFPVBQESA-N
    • A50120
    • AM82773
    • STR03229
    • EN300-1167130
    • AKOS006342996
    • Q27454596
    • 104531-20-6
    • MFCD00270363
    • AC-7943
    • CS-W022752
    • DTXSID30937335
    • SCHEMBL43594
    • J-001192
    • 4-Cyano-D-Phenylalanine
    • MDL: MFCD00270363
    • Inchi: 1S/C10H10N2O2/c11-6-8-3-1-7(2-4-8)5-9(12)10(13)14/h1-4,9H,5,12H2,(H,13,14)/t9-/m0/s1
    • InChI Key: KWIPUXXIFQQMKN-VIFPVBQESA-N
    • SMILES: OC([C@H](CC1C=CC(C#N)=CC=1)N)=O

Computed Properties

  • Exact Mass: 190.07400
  • Monoisotopic Mass: 190.074
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 14
  • Rotatable Bond Count: 3
  • Complexity: 248
  • 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: -1.4
  • Topological Polar Surface Area: 87.1

Experimental Properties

  • Color/Form: No data available
  • Density: 1.28
  • Melting Point: No data available
  • Boiling Point: 394.1±37.0 °C at 760 mmHg
  • Flash Point: 192.1±26.5 °C
  • Refractive Index: 1.595
  • Water Partition Coefficient: Slightly soluble in water.
  • PSA: 87.11000
  • LogP: 1.21298
  • Solubility: Slightly soluble in water.

L-(S)-4-Cyanophenylalanine Customs Data

  • HS CODE:2926909090
  • Customs Data:

    China Customs Code:

    2926909090

    Overview:

    2926909090 Other nitrile based compounds. VAT:17.0% Tax refund rate:9.0% Regulatory conditions:nothing MFN tariff:6.5% general tariff:30.0%

    Declaration elements:

    Product Name, component content, use to

    Summary:

    HS:2926909090 other nitrile-function compounds VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:6.5% General tariff:30.0%

L-(S)-4-Cyanophenylalanine Pricemore >>

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L-(S)-4-Cyanophenylalanine Production Method

Additional information on L-(S)-4-Cyanophenylalanine

Introduction to L-(S)-4-Cyanophenylalanine (CAS No. 167479-78-9)

L-(S)-4-Cyanophenylalanine, identified by the Chemical Abstracts Service Number (CAS No.) 167479-78-9, is a specialized amino acid derivative that has garnered significant attention in the field of pharmaceutical and biochemical research. This compound, characterized by its chiral center and cyano-substituted phenyl group, exhibits unique chemical and biological properties that make it a valuable candidate for various applications, particularly in drug development and enzyme inhibition studies.

The molecular structure of L-(S)-4-Cyanophenylalanine consists of an alanine backbone with a cyanophenyl side chain. The presence of the (S)-configuration at the chiral center imparts specific stereospecificity, which is crucial for its biological activity. This stereochemistry influences how the compound interacts with biological targets, making it a promising candidate for designing enantiopure drugs that exhibit higher efficacy and fewer side effects compared to racemic mixtures.

In recent years, there has been a growing interest in the development of chiral auxiliaries and ligands for asymmetric synthesis. L-(S)-4-Cyanophenylalanine has been explored as a building block in the synthesis of complex molecules due to its ability to induce high enantiomeric excess in catalytic processes. Its incorporation into peptide mimetics and protease inhibitors has shown promising results in preclinical studies, particularly in targeting enzymes involved in inflammatory and infectious diseases.

One of the most compelling applications of L-(S)-4-Cyanophenylalanine is in the field of protease inhibition. Proteases are enzymes that play a critical role in various physiological processes, including digestion, blood clotting, and immune responses. Dysregulation of protease activity is associated with several diseases, such as cancer, arthritis, and HIV/AIDS. The cyanophenyl group in L-(S)-4-Cyanophenylalanine provides a unique interaction surface that can be tailored to bind specifically to target proteases. For instance, studies have demonstrated its potential as an inhibitor of matrix metalloproteinases (MMPs), which are involved in tissue degradation and remodeling.

Moreover, the pharmaceutical industry has leveraged L-(S)-4-Cyanophenylalanine to develop novel antibiotics and antiviral agents. The cyano group enhances the compound's ability to interact with bacterial enzymes and viral proteases, thereby disrupting their function. This property has been particularly useful in designing drugs that target resistant strains of bacteria, where traditional antibiotics have shown limited efficacy.

Recent advancements in computational chemistry have further highlighted the utility of L-(S)-4-Cyanophenylalanine. Molecular modeling studies have revealed its potential as a scaffold for drug discovery programs. By integrating virtual screening techniques with experimental validation, researchers have been able to identify lead compounds that incorporate L-(S)-4-Cyanophenylalanine as a key structural motif. These efforts have led to the identification of several promising candidates for further development into therapeutic agents.

The synthesis of L-(S)-4-Cyanophenylalanine itself presents an interesting challenge due to its stereochemical complexity. Traditional synthetic routes often require multi-step processes involving chiral resolution or asymmetric catalysis. However, recent innovations in biocatalysis have enabled more efficient production methods using engineered enzymes that selectively produce the desired enantiomer. This biotechnological approach not only improves yield but also reduces environmental impact by minimizing waste generation.

In conclusion, L-(S)-4-Cyanophenylalanine (CAS No. 167479-78-9) represents a significant advancement in the field of chiral chemistry and drug development. Its unique structural features and biological activities make it a versatile tool for researchers exploring new therapeutic strategies. As our understanding of molecular interactions continues to evolve, compounds like L-(S)-4-Cyanophenylalanine will undoubtedly play a pivotal role in shaping the future of medicine.

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