Boc-2,3-Difluoro-D-Phenylalanine is an amino acid derivative in which the phenylalanine backbone bears two fluorine atoms at the 2- and 3-positions of the side-chain carbon framework, and the amino acid is provided in the D stereochemical form. The molecule contains a carboxyl group and an N-terminus protected by a Boc (tert-butoxycarbonyl) group, with the fluorinated side-chain imparting increased electronegativity and altered steric/electronic character relative to unmodified phenylalanine. As a protected, fluorinated D-phenylalanine analogue, it is used in peptide and peptidomimetic synthesis and structure-activity or chemical biology studies where incorporation of a difluorinated aromatic residue enables controlled modulation of side-chain properties and analytical differentiation.
CAT No: CP12605
Boc-2,3-Difluoro-D-Phenylalanine is a D-configured, non-proteinogenic amino acid building block bearing a Boc-protected amino group and a 2,3-difluoro-substituted backbone adjacent to the side-chain. The difluorination provides a distinctive electronic and steric environment that is frequently leveraged in peptidomimetic and medicinal chemistry programs to probe structure-activity relationships and backbone effects. As a protected amino acid, it is commonly used as a defined intermediate for assembling fluorinated peptide-like structures where stereochemical control and synthetic handle compatibility are required.
1. Peptidomimetic Peptide Synthesis
Boc-2,3-Difluoro-D-Phenylalanine supports the preparation of fluorinated peptidomimetics and modified peptide segments used in custom peptide synthesis and lead-optimization workflows. Researchers incorporate this D-amino acid building block to introduce a difluoro backbone motif next to the stereocenter, enabling systematic SAR studies on conformational preferences, backbone polarity, and local hydrogen-bonding patterns in peptide-like scaffolds. The Boc protection at the amino terminus aligns with standard protected-amino-acid handling practices for segment coupling, helping teams generate well-defined analog series for downstream biological and biophysical evaluation.
2. Medicinal Chemistry SAR Building Block
Boc-2,3-Difluoro-D-Phenylalanine is frequently used in medicinal chemistry to construct analog libraries where fluorinated amino acid substitutions are used as a rational design element. Medicinal chemistry groups value the fixed D-configuration and the 2,3-difluoro substitution pattern because these features can meaningfully alter physicochemical properties relative to non-fluorinated analogs, while keeping the aromatic side chain consistent for focused comparisons. In practice, the compound serves as a controlled intermediate for synthesizing peptide-like inhibitors, constrained peptidomimetics, and other fluorinated backbone analogs during structure-activity relationship campaigns.
3. Pharmaceutical Intermediate Development
Boc-2,3-Difluoro-D-Phenylalanine is also used as a specialized pharmaceutical intermediate for manufacturing fluorinated amino acid derivatives and peptide-building segments in industrial and process-development settings. Teams developing fluorinated candidates rely on amino-acid-level intermediates to ensure stereochemical fidelity and reproducible incorporation into larger synthetic sequences. The Boc-protected format supports robust intermediate handling and downstream coupling into more complex structures, making this reagent relevant for scale-up-oriented workflows where defined building blocks reduce variability across analog batches.
4. Chiral Fluorinated Amino Acid Libraries
Boc-2,3-Difluoro-D-Phenylalanine is commonly selected for assembling chiral, fluorinated amino acid libraries used in chemical biology and medicinal chemistry discovery. By providing a D-stereocenter combined with a 2,3-difluoro backbone motif and a protected amino group, it enables researchers to generate parallel sets of fluorinated analogs that differ in stereochemistry or substitution pattern while maintaining a consistent aromatic side chain. Such libraries are used to support comparative studies of backbone-modified peptide analogs, where the ability to vary stereochemical and fluorination elements in a controlled manner is central to experimental design.
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