Cas no 204260-38-8 (Fmoc-4-methyl-D-phenylalanine)

Fmoc-4-methyl-D-phenylalanine is a protected amino acid derivative widely used in peptide synthesis, particularly in solid-phase peptide synthesis (SPPS). The Fmoc (9-fluorenylmethoxycarbonyl) group serves as a temporary protecting group for the amine functionality, enabling selective deprotection under mild basic conditions. The 4-methyl substituent on the phenyl ring enhances steric and electronic properties, which can influence peptide conformation and stability. This D-configuration amino acid is valuable for introducing chirality and modifying peptide backbones to improve resistance to enzymatic degradation. Its high purity and compatibility with standard Fmoc-chemistry protocols make it a reliable choice for research and pharmaceutical applications requiring structurally modified peptides.
Fmoc-4-methyl-D-phenylalanine structure
Fmoc-4-methyl-D-phenylalanine structure
Product Name:Fmoc-4-methyl-D-phenylalanine
CAS No:204260-38-8
MF:C25H23NO4
MW:401.45442700386
MDL:MFCD00270196
CID:66687
PubChem ID:2756073
Update Time:2025-10-24

Fmoc-4-methyl-D-phenylalanine Chemical and Physical Properties

Names and Identifiers

    • Fmoc-4-methyl-D-phenylalanine
    • Fmoc-D-Phe(4-Me)-OH
    • Fmoc-D-4-Methylphe
    • Fluorenylmethoxycarbonyl-D-4-methylphenylalanine
    • FMOC-D-4-METHYLPHENYLALANINE
    • Fmoc-p-Me-D-Phe-OH
    • 4-Methyl-D-phenylalanine, N-FMOC protected
    • AmbotzFAA1683
    • Fmoc-L-phe(4-me)-OH
    • FMOC-P-ME-D-PHENYLALANINE
    • Fmoc-4-Methy-D-Phenylalanine
    • (2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-(4-methylphenyl)propanoic acid
    • DTXSID20373223
    • SCHEMBL118250
    • N-FLUORENEMETHOXYCARBONYL-L-4-METHYL PHENYLALANINE
    • MFCD00270196
    • UXLHLZHGQPDMJQ-HSZRJFAPSA-N
    • (2R)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-(4-methylphenyl)propanoic acid
    • CS-0153092
    • J-013304
    • AKOS015837378
    • A50177
    • (R)-2-(((9H-FLUOREN-9-YL)METHOXY)CARBONYLAMINO)-3-P-TOLYLPROPANOIC ACID
    • AM83433
    • PS-12014
    • AC-9930
    • 204260-38-8
    • D-Phenylalanine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-4-methyl-
    • EN300-3421786
    • (2R)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-3-(4-methylphenyl)propanoic acid
    • MDL: MFCD00270196
    • Inchi: 1S/C25H23NO4/c1-16-10-12-17(13-11-16)14-23(24(27)28)26-25(29)30-15-22-20-8-4-2-6-18(20)19-7-3-5-9-21(19)22/h2-13,22-23H,14-15H2,1H3,(H,26,29)(H,27,28)/t23-/m1/s1
    • InChI Key: UXLHLZHGQPDMJQ-HSZRJFAPSA-N
    • SMILES: O(C(N[C@@H](C(=O)O)CC1C=CC(C)=CC=1)=O)CC1C2C=CC=CC=2C2=CC=CC=C12

Computed Properties

  • Exact Mass: 401.16300
  • Monoisotopic Mass: 401.163
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 5
  • Heavy Atom Count: 30
  • Rotatable Bond Count: 8
  • Complexity: 578
  • 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
  • Topological Polar Surface Area: 75.6A^2
  • Surface Charge: 0
  • Tautomer Count: 2
  • XLogP3: 5

Experimental Properties

  • Color/Form: No data avaiable
  • Density: 1.3±0.1 g/cm3
  • Melting Point: 168 oC
  • Boiling Point: 629.1±55.0 °C at 760 mmHg
  • Flash Point: 334.3±31.5 °C
  • PSA: 75.63000
  • LogP: 4.92030
  • Vapor Pressure: 0.0±1.9 mmHg at 25°C
  • Specific Rotation: 31 o (c=1,DMF)

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Fmoc-4-methyl-D-phenylalanine Suppliers

Tiancheng Chemical (Jiangsu) Co., Ltd
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(CAS:204260-38-8)FMOC-D-4-甲基苯丙氨酸
Order Number:LE2468613
Stock Status:in Stock
Quantity:25KG,200KG,1000KG
Purity:99%
Pricing Information Last Updated:Friday, 20 June 2025 12:38
Price ($):discuss personally

Additional information on Fmoc-4-methyl-D-phenylalanine

Professional Introduction to Fmoc-4-methyl-D-phenylalanine (CAS No. 204260-38-8)

Fmoc-4-methyl-D-phenylalanine, with the chemical identifier CAS No. 204260-38-8, is a crucial intermediate in the field of peptidomimetics and pharmaceutical synthesis. This compound, featuring an Fmoc (fluorenylmethyloxycarbonyl) protecting group and a chiral D-amino acid backbone, has garnered significant attention due to its utility in constructing complex peptide-based therapeutics.

The Fmoc protecting group is particularly noteworthy for its stability under basic conditions, making it an ideal choice for solid-phase peptide synthesis (SPPS). This property allows for efficient and controlled assembly of peptide chains, which is essential for the development of biologics such as antibodies and enzyme inhibitors. The incorporation of 4-methyl substituent in the phenyl ring of D-phenylalanine enhances the steric hindrance and improves the solubility profile of the resulting peptides, thereby facilitating their biological activity.

In recent years, there has been a surge in research focused on peptidomimetics—molecules that mimic the structure and function of natural peptides but with improved pharmacokinetic properties. Fmoc-4-methyl-D-phenylalanine plays a pivotal role in this domain by serving as a building block for designing novel peptidomimetics. These peptidomimetics are being explored for their potential in treating various diseases, including cancer, inflammation, and neurodegenerative disorders.

One of the most compelling applications of Fmoc-4-methyl-D-phenylalanine is in the development of protease inhibitors. Proteases are enzymes that play a critical role in numerous biological processes, and their overactivity or misregulation is associated with several diseases. By designing peptidomimetics that specifically target these proteases, researchers aim to develop highly selective and potent inhibitors. For instance, studies have shown that peptidomimetics incorporating Fmoc-protected D-amino acids exhibit enhanced binding affinity and stability against target proteases compared to their natural peptide counterparts.

The use of Fmoc-4-methyl-D-phenylalanine also extends to the field of vaccine development. Peptide-based vaccines are designed to elicit an immune response by mimicking pathogenic antigens. The structural integrity and biological activity of these vaccines can be significantly improved by incorporating chiral amino acids like D-phenylalanine. This modification not only enhances vaccine efficacy but also reduces potential side effects.

Advances in synthetic methodologies have further expanded the utility of Fmoc-4-methyl-D-phenylalanine. Modern SPPS techniques, coupled with automated synthesizers, have made it possible to construct complex peptides with high precision and yield. Additionally, innovations in computational chemistry have enabled researchers to predict and optimize the properties of peptidomimetics before experimental synthesis, thereby accelerating drug discovery pipelines.

The growing interest in green chemistry has also influenced the synthesis of Fmoc-4-methyl-D-phenylalanine. Researchers are increasingly adopting sustainable practices to minimize waste and reduce environmental impact. For example, solvent-free reactions and biocatalytic approaches are being explored as alternatives to traditional synthetic methods. These advancements not only align with global sustainability goals but also enhance cost-effectiveness and scalability.

In conclusion, Fmoc-4-methyl-D-phenylalanine (CAS No. 204260-38-8) is a versatile and indispensable compound in modern pharmaceutical research. Its unique combination of protective group functionality and chiral purity makes it an invaluable tool for constructing advanced peptidomimetics. As research continues to uncover new therapeutic applications, the demand for high-quality intermediates like Fmoc-4-methyl-D-phenylalanine is expected to grow exponentially.

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Tiancheng Chemical (Jiangsu) Co., Ltd
(CAS:204260-38-8)FMOC-D-4-甲基苯丙氨酸
LE2468613
Purity:99%
Quantity:25KG,200KG,1000KG
Price ($):Inquiry
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