3,5-Difluoro-DL-tyrosine is a fluorinated, non-proteinogenic tyrosine derivative in which the phenolic side chain of tyrosine is substituted with two fluorine atoms at the 3 and 5 positions. The molecule contains both an α-amino group and a carboxyl group, and it bears a substituted phenol that can participate in hydrogen-bonding and electrophilic aromatic substitution chemistry, with the "DL" designation indicating a racemic mixture of stereochemical forms at the α-carbon. As a halogenated aromatic amino acid, it is commonly used in peptide synthesis and structure-activity or binding studies where fluorine substitution supports NMR/analytical characterization and side-chain electronic modulation.
CAT No: CP18103
3,5-Difluoro-DL-tyrosine is a fluorinated tyrosine analog featuring a DL stereochemical mixture and two fluorine atoms on the phenolic ring (3,5-difluoro substitution). This aromatic fluorination provides a distinctive electronic and steric environment while retaining the phenolic hydroxyl functionality, making the compound a useful building block for medicinal chemistry and fluorinated aromatic SAR studies. Researchers also leverage its tyrosine-like scaffold to probe how ring substitution patterns influence peptide and small-molecule behavior, including physicochemical properties and aromatic interactions.
1. Medicinal Chemistry SAR Studies
3,5-Difluoro-DL-tyrosine is used in structure-activity relationship (SAR) campaigns to introduce a fluorinated phenolic aromatic motif into tyrosine-derived analogs and peptidomimetics. Medicinal chemistry groups commonly incorporate this scaffold to examine how 3,5-difluoro substitution modulates aromatic electronics and hydrogen-bonding patterns associated with the phenolic hydroxyl, supporting rational optimization of lead series. Its DL form is often selected during early-stage synthesis planning when the stereochemical outcome is evaluated downstream by separation or by assessing biological activity across stereoisomers, and when the phenolic group is intended to remain available for further derivatization.
2. Fluorinated Peptide Building Block
3,5-Difluoro-DL-tyrosine is applied as an amino acid building block for preparing fluorinated peptides and peptide fragments where a tyrosine-like residue with ring fluorination is required. Peptide synthesis teams use this compound to generate analogs that differ from native tyrosine by the 3,5-difluoro substitution pattern, enabling comparative studies of how aromatic fluorination affects conformation, stability, and interaction profiles in peptide contexts. The presence of the phenolic hydroxyl also supports downstream functionalization strategies when researchers need to control derivatization of the side chain after peptide assembly.
3. Phenolic Derivatization Intermediates
3,5-Difluoro-DL-tyrosine serves as a practical intermediate for producing phenol-functional derivatives used in chemical biology and materials-adjacent research workflows. Synthetic chemists frequently target the phenolic hydroxyl for conversion into protected or activated forms that can be carried into subsequent coupling steps, allowing the 3,5-difluoro aromatic ring to be maintained as a defined motif. This approach is particularly useful when the fluorinated ring is required as a stable, chemically informative substituent for later analytical tracking, derivatization, or incorporation into larger molecular frameworks.
4. Analytical Reference Standards
3,5-Difluoro-DL-tyrosine is also used as a defined analytical reference material in method development and characterization workflows involving fluorinated aromatic amino acid motifs. Analytical chemistry teams employ it to support LC-MS and related characterization of fluorinated peptide intermediates, reaction mixtures, and final fluorinated products where the 3,5-difluoro-phenol signature is a useful identifier. The DL stereochemical mixture can be advantageous when the analytical goal is to track the presence of the fluorinated tyrosine analog regardless of stereoisomeric composition, especially during early process development and impurity profiling.
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