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Best 3-Fluoro-L-Phenylalanine丨CAS 19883-77-3
3-Fluoro-L-Phenylalanine is a fluorinated derivative of L-phenylalanine featuring a fluorine atom at the meta position of the aromatic ring. As a non-proteinogenic amino acid, it is used in peptide synthesis, medicinal chemistry, and specialized organic synthesis. The fluorine substituent can influence the electronic characteristics and molecular interactions of the aromatic side chain, while the L-configuration supports the preparation of stereochemically defined compounds. With its free amino and carboxyl groups, 3-Fluoro-L-Phenylalanine provides a versatile starting material for preparing modified peptides, fluorinated amino acid derivatives, and 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-/m0/s1 |
| InChI Key | VWHRYODZTDMVSS-QMMMGPOBSA-N |
| Smiles | C1=CC(=CC(=C1)F)C[C@@H](C(=O)O)N |
| EC No. | 670-961-4 |
| MDL No. | MFCD00066450 |
| PubChem CID | 716315 |
Applications
Applications in Peptide Synthesis
3-Fluoro-L-Phenylalanine can be incorporated into peptide sequences to introduce a meta-fluorinated aromatic residue. Replacing a conventional phenylalanine residue with this analogue may influence peptide conformation, local electronic properties, and interactions with surrounding molecular groups. It is therefore useful in the preparation of modified peptides and peptide analogues for investigating structure–activity relationships and exploring the effects of fluorinated amino acid substitution.
Applications in Medicinal Chemistry Research
Fluorinated amino acids are widely used in medicinal chemistry because fluorine substitution can modify molecular properties without substantially increasing molecular size. 3-Fluoro-L-Phenylalanine serves as a building block for synthesizing peptide-based compounds and other molecules containing a meta-fluorinated aromatic group. Researchers can use it to investigate how fluorination affects molecular interactions, physicochemical properties, and biological activity during compound optimization and structure–activity relationship studies.
Applications in Protein and Biochemical Research
3-Fluoro-L-Phenylalanine can support research involving amino acid analogues, protein structure, and molecular recognition. Its fluorinated aromatic side chain provides distinct electronic characteristics that may be useful in selected analytical and structural research workflows. Depending on the experimental system, the compound may be investigated in studies of protein–ligand interactions and the effects of amino acid substitution on molecular behavior.
Applications in Organic Synthesis
The amino and carboxyl groups of 3-Fluoro-L-Phenylalanine enable a range of standard amino acid transformations, including protection, esterification, and amide formation. Its fluorinated aromatic ring can be retained as a structural feature during subsequent synthetic steps, supporting the preparation of diverse intermediates and specialty compounds. This makes it a useful starting material for research projects requiring an L-configured amino acid with a meta-fluorinated phenyl group.
