3-Fluoro-D-tyrosine is a fluorinated, non-proteinogenic amino acid derivative in the tyrosine family, featuring a para-fluorinated phenolic side chain attached to a D-configured amino acid backbone. The molecule contains a free amino group and a carboxyl group and bears a phenolic aromatic ring where the fluorine substituent modifies electronic properties and can influence hydrogen-bonding and aromatic interactions relative to unfluorinated tyrosine. It is used in peptide and protein structure-function studies, chemical biology labeling strategies, and analytical method development where fluorinated amino acid analogues provide a defined handle for NMR, MS, or structure-based characterization.
CAT No: CP18502
3-Fluoro-D-tyrosine is a D-configured tyrosine analog bearing a fluorine substituent on the aromatic ring, providing a chemically defined handle for studying halogen effects on aromatic electronics, hydrogen bonding patterns, and structure-activity relationships. As a non-proteinogenic amino acid building block, it is commonly used in peptide and peptidomimetic synthesis where stereochemistry and side-chain substitution are critical for downstream binding and analytical readouts. The aryl fluorine also offers a useful site for NMR-based characterization and for designing fluorine-containing analogs used in medicinal chemistry optimization.
1. Peptide And Peptidomimetic Synthesis
3-Fluoro-D-tyrosine is used as an amino acid building block for incorporating a fluorinated, D-configured aromatic side chain into short peptides and peptidomimetics during custom peptide synthesis. Researchers select the fluorinated tyrosine analog to introduce a defined change in aromatic electronics and steric environment relative to standard tyrosine, enabling structure-activity relationship studies in ligand-binding and receptor/target interaction assays. The D-configuration supports workflows that probe stereochemical effects on conformation, protease stability trends, and overall scaffold behavior in chemical biology and medicinal chemistry programs.
2. Medicinal Chemistry SAR Probes
3-Fluoro-D-tyrosine is frequently employed in medicinal chemistry to generate fluorinated analog series for SAR (structure-activity relationship) optimization, where ring fluorination provides a controllable perturbation of physicochemical properties and interaction motifs. Medicinal chemistry teams use this building block to prepare site-specific fluorinated peptides or peptidomimetic fragments that can be compared directly against non-fluorinated counterparts in binding and functional screening campaigns. The defined D-stereochemistry further supports the design of stereochemically constrained or non-natural scaffolds used to map the contribution of side-chain orientation and aromatic substitution to observed activity trends, while also enabling consistent analytical comparison across analogs.
3. Fluorine NMR And Analytical Characterization
3-Fluoro-D-tyrosine is well suited for analytical method development and structural characterization workflows that benefit from a defined 19F signal in the aromatic side chain. Chemical biology and analytical chemistry groups incorporate the fluorinated amino acid into peptides or model compounds to create 19F-containing standards for NMR-based monitoring of synthesis, purity assessment of fluorinated intermediates, and verification of incorporation at specific positions. The presence of a single fluorine site supports straightforward spectroscopic readouts and helps streamline confirmation of analog identity in fluorinated SAR libraries, where distinguishing closely related structures is often a key practical requirement.
4. Protein Engineering Mimetic Design
3-Fluoro-D-tyrosine is used in protein engineering and chemical protein design efforts where non-natural, fluorinated residues are introduced into peptide-based mimics or engineered binding domains to interrogate aromatic interaction geometry and electronic effects. Researchers commonly apply this building block in the preparation of fluorine-containing peptide segments used as probes in protein interaction studies, domain mapping, or scaffold optimization, especially when a stereodefined D-amino acid is required to control local conformation. In these workflows, the fluorinated tyrosine side chain provides a chemically stable aromatic modification that supports comparative studies across analogs and facilitates spectroscopic tracking when 19F readouts are part of the experimental plan.
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