3,5-Difluoro-L-tyrosine is a fluorinated, proteinogenic amino acid derivative belonging to the tyrosine family, featuring a phenolic aromatic side chain substituted with two fluorine atoms at the 3- and 5-positions. The molecule contains a free α-amino group and a carboxylic acid, and it bears the L-tyrosine stereochemical configuration as indicated by the name, with the fluorinated phenol providing altered electronic properties relative to unmodified tyrosine. As a chemically defined tyrosine analogue, it is used in peptide and protein engineering and in structure-function studies where side-chain fluorination can support chemical probing, labeling strategies, and analytical method development.
CAT No: CP18101
CAS No:73246-30-7
Synonyms/Alias:3,5-Difluoro-L-Tyrosine;73246-30-7;SCHEMBL296874;H-Tyr(3,5-F2)-OH;CTK1C4178;ZINC6091244;AM83559;AM009322;KB-28693;SC-11005;(2S)-2-AMINO-3-(3,5-DIFLUORO-4-HYDROXYPHENYL)PROPANOICACID;F2Y
3,5-Difluoro-L-tyrosine is a fluorinated, proteinogenic amino acid analog derived from L-tyrosine, featuring two fluorine atoms on the phenolic ring that tune electronic properties while preserving the tyrosine-like aromatic hydroxyl functionality. This side-chain retains the phenolic group used in many tyrosine chemistry workflows, while the difluoro substitution provides a distinctive handle for spectroscopic and analytical differentiation. In peptide and medicinal chemistry contexts, it is used to probe structure-activity relationships, improve chemical tractability for labeling strategies, and introduce a fluorinated aromatic residue into synthetic sequences.
1. Peptide Building Block
3,5-Difluoro-L-tyrosine is used as a defined amino acid building block for custom peptide synthesis where a tyrosine analog is required to study how ring electronics and fluorination affect conformation, local interactions, and chemical stability of peptide motifs. Peptide chemists incorporate this residue into solution-phase or solid-phase workflows to generate fluorinated peptide standards and analog libraries for downstream biological assays and chemical biology experiments, while maintaining the phenolic hydroxyl as the key functional group for residue-level chemistry. The difluoro substitution provides a residue that is readily distinguishable from native tyrosine in analytical characterization of peptide products.
2. Medicinal Chemistry SAR Probing
3,5-Difluoro-L-tyrosine supports medicinal chemistry and peptidomimetic development efforts that require aromatic fluorination to modulate physicochemical behavior and to enable clearer analytical tracking of analogs in structure-activity relationship (SAR) studies. Medicinal chemistry teams use fluorinated tyrosine analogs to prepare series of peptide-like compounds and intermediates where the aromatic ring substitution pattern is systematically varied, while the phenolic hydroxyl helps maintain a tyrosine-like hydrogen-bonding motif. This product is also used when researchers need a chemically defined aromatic residue for mechanistic or property-focused studies, including comparative stability and reactivity profiling across tyrosine variants.
3. Fluorinated Residue Labeling Standards
3,5-Difluoro-L-tyrosine is widely used to prepare analytical standards and reference materials for LC-MS method development and quantitation workflows involving fluorinated aromatic amino acids and peptides. The presence of two ring fluorines creates a strong, characteristic mass signature and supports unambiguous identification of this residue-containing species in complex mixtures, which is valuable for method validation, impurity profiling, and comparative analysis of tyrosine analog panels. Analytical chemistry groups and peptide characterization labs also use it to benchmark fragmentation behavior and to confirm incorporation of fluorinated tyrosine analogs during peptide synthesis and purification.
4. Chemical Biology Probe Residue
3,5-Difluoro-L-tyrosine is applied in chemical biology workflows that require a tyrosine-derived aromatic residue with a chemically informative substitution pattern for tracking and characterization of labeled or modified biomolecular constructs. Researchers incorporate this fluorinated tyrosine analog into peptides used as probes to study residue-level effects on binding-site microenvironments, interaction mapping, or conformational preferences, while retaining the phenolic hydroxyl for compatibility with tyrosine-oriented derivatization strategies when needed. The difluoro aromatic ring helps distinguish probe-containing constructs from native-sequence counterparts during analytical readouts, supporting clearer interpretation of residue-specific experiments.
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