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2-Fluoro-D-phenylalanine丨CAS 97731-02-7
2-Fluoro-D-phenylalanine is a fluorinated derivative of D-phenylalanine featuring a fluorine atom at the ortho position of the aromatic ring. As a non-proteinogenic amino acid, it is used as a building block in peptide synthesis, medicinal chemistry, and specialized organic synthesis. The D-configuration provides a stereochemical alternative to the corresponding L-isomer, while the fluorine substituent can influence electronic properties and molecular interactions. Its amino and carboxyl groups offer versatile reaction sites for further derivatization, making it useful for preparing modified amino acids, peptide analogues, and research compounds.
Chemical Identifiers
| InChI | InChI=1S/C9H10FNO2/c10-7-4-2-1-3-6(7)5-8(11)9(12)13/h1-4,8H,5,11H2,(H,12,13)/t8-/m1/s1 |
| InChI Key | NYCRCTMDYITATC-MRVPVSSYSA-N |
| Smiles | C1=CC=C(C(=C1)C[C@H](C(=O)O)N)F |
| EC No. | |
| MDL No. | MFCD00066447 |
| PubChem CID | 716322 |
Applications
Applications in Peptide Synthesis
2-Fluoro-D-phenylalanine can be incorporated into peptide sequences to introduce a D-configured, fluorinated aromatic residue. The inclusion of D-amino acids may affect peptide conformation, resistance to enzymatic degradation, and interactions with biological targets, depending on the sequence. The ortho-fluorine substituent adds another structural variable for peptide design, making this compound relevant to research involving modified peptides, peptide analogues, and structure–activity relationship studies.
Applications in Medicinal Chemistry Research
Fluorinated amino acids are valuable in medicinal chemistry because fluorine substitution can alter molecular electronics, lipophilicity, and metabolic behavior. 2-Fluoro-D-phenylalanine provides a combination of D-stereochemistry and ortho-fluorination for exploring these effects in peptide-based compounds and other molecular structures. Researchers can use it as a building block to investigate how stereochemical configuration and aromatic substitution influence molecular properties and biological activity.
Applications in Protein and Biochemical Research
2-Fluoro-D-phenylalanine may support studies involving amino acid analogues, molecular recognition, and the effects of nonstandard residues on biological systems. Its fluorinated aromatic group provides distinct electronic characteristics that may be useful in selected analytical or structural research workflows. Because the D-configuration can affect recognition by enzymes and biological systems, its use in a particular experimental model should be evaluated according to the research objective and incorporation method.
Applications in Organic Synthesis
The amino and carboxyl functionalities of 2-Fluoro-D-phenylalanine support common amino acid transformations, including protection, esterification, and amide formation. The fluorinated aromatic ring can be retained as a structural feature during subsequent synthetic steps, allowing the preparation of diverse intermediates and specialty compounds. This makes the compound a useful starting material for research projects requiring a stereochemically defined fluorinated amino acid.
