3,5-Difluoro-D-tyrosine is a fluorinated, non-proteinogenic tyrosine analogue featuring a phenolic aromatic ring bearing two fluorine substituents at the 3- and 5-positions and a D-configured α-amino acid framework. The molecule contains a free α-amino group and a free carboxyl group alongside a substituted phenol side chain, where the fluorination modulates the ring electronics and hydrogen-bonding behavior relative to unmodified tyrosine. As a structurally defined amino acid derivative, it is used in peptide and protein engineering workflows and in chemical biology or analytical studies that require incorporation or detection of fluorinated aromatic residues for structure-activity investigations, molecular labeling, or mass spectrometry-based characterization.
CAT No: CP18102
3,5-Difluoro-D-tyrosine is a fluorinated, D-configured tyrosine analog in which two ring positions are substituted with fluorine atoms, creating a distinct electronic and steric environment relative to natural tyrosine. This non-proteinogenic amino acid building block is frequently used in peptide and medicinal chemistry programs where fluorination is leveraged to tune aromatic behavior, improve metabolic stability profiles by blocking common modification sites, and support structure-activity relationship studies. Its phenolic side chain and defined stereochemistry make it a practical reagent for downstream incorporation into synthetic peptides and for preparing analogs used in chemical biology and analytical characterization workflows.
1. Peptide Analog Synthesis
3,5-Difluoro-D-tyrosine is used as a defined amino acid building block for assembling D-amino-acid-containing peptides and peptide analogs in custom peptide synthesis projects. Researchers incorporate this fluorinated tyrosine mimic to evaluate how altered aromatic electronics and the difluoro substitution pattern influence peptide conformation, binding interactions, and structure-property relationships in lead optimization. The D-configuration supports the preparation of stereochemically controlled peptide libraries aimed at probing sequence dependence and protease resistance trends in peptide design studies, while the phenolic side chain provides a chemically consistent aromatic functionality for comparative studies against other tyrosine variants.
2. Medicinal Chemistry SAR Building Block
3,5-Difluoro-D-tyrosine supports medicinal chemistry and peptidomimetic development by enabling systematic SAR (structure-activity relationship) work around a fluorinated aromatic residue. Medicinal chemistry groups use this building block to generate analog series where the difluoro pattern modulates physicochemical properties and changes the aromatic substitution environment without changing the overall amino acid backbone identity. This makes it particularly useful for preparing non-natural residue variants used in binding and selectivity profiling campaigns, as well as for producing reference compounds for analytical method development tied to fluorinated peptide or peptidomimetic scaffolds.
3. Chemical Biology Probe Residue
3,5-Difluoro-D-tyrosine is applied in chemical biology workflows that require an aromatic residue with a distinct, fluorinated signature for tracking and comparative studies in labeled or analog-based systems. Scientists use fluorinated tyrosine analogs as site-specific substitutes within peptide probes to study structure-function relationships while maintaining a tyrosine-like aromatic handle for downstream conjugation strategies when needed. In practice, this residue is often selected when researchers want a chemically stable aromatic motif that differs from natural tyrosine, enabling discrimination of probe-containing constructs during purification and analytical characterization by LC-MS and related fluorinated-compound profiling approaches.
4. LC-MS Reference Compound Preparation
3,5-Difluoro-D-tyrosine is also used for analytical reference preparation in workflows that quantify or monitor fluorinated amino acid and peptide components by mass spectrometry. Analytical chemistry teams prepare standards and calibration materials based on this defined difluoro-D-tyrosine residue to support method development, impurity tracking, and identity confirmation for fluorinated peptide analogs. The presence of two fluorine atoms provides a characteristic mass shift and fragmentation behavior that can improve interpretability when distinguishing closely related aromatic amino acid variants, making the compound valuable for routine QA/QC-style analytical development in research and industrial synthesis settings.
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