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High Quality 4-Fluoro-D-phenylalanine丨CAS 18125-46-7
4-Fluoro-D-Phenylalanine (CAS 18125-46-7) is a fluorinated aromatic amino acid used as a building block in peptide synthesis, medicinal chemistry, and organic synthesis. It features a D-phenylalanine backbone with a fluorine atom at the para (4-) position of the phenyl ring. Its defined stereochemistry and fluorinated aromatic side chain make it useful for preparing modified peptides and specialized compounds for research and development.
Chemical Identifiers
| InChI | InChI=1S/C9H10FNO2/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,8H,5,11H2,(H,12,13)/t8-/m1/s1 |
| InChI Key | XWHHYOYVRVGJJY-MRVPVSSYSA-N |
| Smiles | C1=CC(=CC=C1C[C@H](C(=O)O)N)F |
| EC No. | 686-379-9 |
| MDL No. | MFCD00063064 |
| PubChem CID | 716314 |
Applications
Applications in Peptide and Amino Acid Chemistry
4-Fluoro-D-Phenylalanine can be incorporated into synthetic peptides to introduce a D-amino acid residue with a para-fluorinated aromatic side chain. Replacing an L-amino acid with its D-counterpart can influence peptide conformation, enzymatic stability, and interactions with biological targets. This compound supports the development of modified peptide sequences and provides researchers with a means of investigating the effects of stereochemical changes and aromatic fluorination on peptide properties.
Applications in Medicinal Chemistry Research
In medicinal chemistry, 4-Fluoro-D-Phenylalanine serves as a building block for synthesizing fluorinated amino acid derivatives, peptide analogues, and other research compounds. The para-fluoro substituent can alter the electronic characteristics of the aromatic ring and may influence lipophilicity, metabolic stability, and molecular recognition. Researchers can use this structural modification to investigate structure–activity relationships and explore potential improvements in candidate-compound properties.
Applications in Pharmaceutical Research
4-Fluoro-D-Phenylalanine is useful in research involving peptide-based compounds, modified amino acid sequences, and biologically active molecule candidates. Its D-configuration offers an alternative stereochemical arrangement for exploring molecular conformation and resistance to enzymatic degradation, while the fluorinated aromatic ring provides an additional structural feature for compound design. Its effects on biological activity and stability depend on the overall molecular structure and should be evaluated experimentally.
Applications in Organic Synthesis
As a functionalized amino acid building block, 4-Fluoro-D-Phenylalanine can be used in multistep organic synthesis to prepare more complex molecules containing a fluorinated aromatic amino acid unit. It is relevant to synthetic routes involving peptide intermediates, specialty amino acid derivatives, and fluorinated compounds. Its defined stereochemistry makes it particularly useful when the configuration of the amino acid residue is important to the target structure.
