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Bulk Supply 3-Fluoro-D-phenylalanine丨CAS 110117-84-5
3-Fluoro-D-Phenylalanine (CAS 110117-84-5) is a fluorinated D-amino acid used as a building block in peptide chemistry, medicinal chemistry, and organic synthesis. It features a fluorine substituent at the 3-position of the phenyl ring and a D-configuration at the alpha carbon. The combination of stereochemical definition and aromatic fluorination makes this compound useful for preparing structurally modified peptides and specialized research intermediates.
Chemical Identifiers
| InChI | InChI=1S/C9H10FNO2/c10-7-3-1-2-6(4-7)5-8(11)9(12)13/h1-4,8H,5,11H2,(H,12,13)/t8-/m1/s1 |
| InChI Key | VWHRYODZTDMVSS-MRVPVSSYSA-N |
| Smiles | C1=CC(=CC(=C1)F)C[C@H](C(=O)O)N |
| EC No. | 686-374-1 |
| MDL No. | MFCD00066449 |
| PubChem CID | 716317 |
Applications
Applications in Peptide Synthesis
3-Fluoro-D-Phenylalanine can be incorporated into peptide sequences to introduce a D-amino acid residue with a fluorinated aromatic side chain. Substituting conventional amino acids with D-amino acids may influence peptide conformation, proteolytic stability, and interactions with biological targets. This compound supports the preparation of modified peptides for laboratory research, peptide design, and structure–activity relationship studies.
Applications in Medicinal Chemistry Research
In medicinal chemistry, 3-Fluoro-D-Phenylalanine serves as a building block for synthesizing fluorinated compounds and peptide analogues. Fluorine substitution can alter the electronic characteristics of the aromatic ring and may affect lipophilicity, metabolic behavior, and molecular recognition. Researchers can use this structural modification to investigate relationships between molecular structure and biological activity.
Applications in Pharmaceutical Research
This amino acid is suitable for research programs involving peptide-based candidates, modified amino acid sequences, and small molecules derived from amino acid intermediates. Its D-configuration provides an alternative stereochemical arrangement for exploring molecular conformation and target interactions, while the fluorinated phenyl group offers an additional structural feature for compound optimization. Its performance and suitability depend on the design of the target molecule and the intended research application.
Applications in Organic Synthesis
3-Fluoro-D-Phenylalanine can also be used as a specialized intermediate in multistep organic synthesis. Its amino acid backbone and fluorinated aromatic ring provide a foundation for preparing more complex molecular structures. It is relevant to research workflows that require defined stereochemistry and selective incorporation of fluorinated amino acid units.
