3-Fluoro-D-Phenylalanine is a non-natural, fluorinated phenylalanine analogue bearing a benzyl side chain substituted with fluorine at the 3-position and a stereochemically specified D-configuration at the alpha carbon. The molecule contains a free amino group and a free carboxyl group, enabling it to behave as an amino acid in coupling chemistry while the aryl fluorine provides a distinct electronic and steric environment for NMR, mass spectrometry, and structure-activity studies. It is used in peptide and amino acid derivative synthesis to introduce fluorinated aromatic residues for chemical biology labeling, conformational or interaction probing, and analytical method development where a defined fluorinated stereochemical motif is required.
CAT No: CP14502
CAS No:110117-84-5
Synonyms/Alias:3-Fluoro-D-phenylalanine;110117-84-5;D-3-fluorophenylalanine;(2R)-2-amino-3-(3-fluorophenyl)propanoicacid;3-fluor-d-phenylalanin;D-3-FLUOROPHE;m-Fluoro-D-phenylalanine;3-FLUORO-D-PHE;SBB063823;(R)-2-AMINO-3-(3-FLUOROPHENYL)PROPANOICACID;2629-54-1;PubChem17963;AC1LEQE9;AC1Q4NBJ;D-3-F-PHE-OH;H-M-FLUORO-D-PHE-OH;KSC497E4F;D-PHE(3-F)-OH;H-D-PHE(3-F)-OH;SCHEMBL288728;CTK3J7242;MolPort-001-775-432;ZINC113787;D-PHENYLALANINE,3-FLUORO-;ANW-59160
3-Fluoro-D-Phenylalanine is a D-configured phenylalanine analog bearing a single fluorine substituent on the aromatic ring, providing a distinct electronic and steric profile relative to native phenylalanine. This non-natural amino acid is frequently used in peptide and medicinal chemistry workflows where fluorinated aromatic residues are leveraged to probe structure-activity relationships, conformational effects, and binding-site interactions. Its stereochemical definition supports incorporation into defined peptide sequences and enables reproducible comparative studies in chemical biology and SAR programs.
1. Fluorinated Peptide Building Block
3-Fluoro-D-Phenylalanine is used as a site-specific amino acid building block for preparing fluorinated peptides and peptide analogs in custom peptide synthesis. Researchers commonly incorporate this residue to introduce a defined fluorinated aromatic side chain, enabling systematic evaluation of how aryl fluorination influences peptide conformation, local hydrophobicity, and interaction patterns within binding interfaces. The D-configuration supports designs that incorporate non-proteinogenic stereochemistry, which is often used to improve resistance to proteolytic degradation in peptide research programs and to generate stereochemically defined analog series for mechanistic or binding studies.
2. Medicinal Chemistry SAR Studies
3-Fluoro-D-Phenylalanine is widely applied in medicinal chemistry and peptidomimetic development as a fluorinated aromatic substituent for structure-activity relationship (SAR) investigations. Medicinal chemistry groups use this analog to modulate electronic properties of the phenyl ring and to create a chemically distinct residue that can be compared directly against non-fluorinated or differently substituted counterparts. The defined D-stereochemistry supports consistent analog generation when researchers are mapping the contribution of stereochemistry and aromatic fluorination to potency trends, selectivity profiles, and binding-site complementarity in lead optimization campaigns.
3. Chemical Biology Binding Probes
3-Fluoro-D-Phenylalanine is used in chemical biology to generate defined fluorinated peptide probes for studying molecular recognition and binding-site environments. By placing a fluorinated aromatic residue at a chosen position, researchers can create probes that provide a distinct chemical signature for downstream characterization and comparative interaction mapping. This amino acid is particularly valuable when probe libraries require stereochemically defined, non-natural residues to separate stereochemical effects from side-chain electronic effects, supporting more interpretable structure-function studies in receptor-ligand, protein-peptide, and biomolecular interaction research.
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