Boc-2,6-Difluoro-L-Phenylalanine is a protected, fluorinated phenylalanine derivative in which the amino group is masked as a Boc carbamate and the aromatic side chain bears two fluorine substituents at the 2 and 6 positions relative to the benzylic carbon. The molecule contains a carboxylic acid functionality and a Boc-protected α-amino group, with the side chain retaining the L-configuration indicated in the name and featuring a difluorinated phenyl ring that alters electronic character and hydrophobic/halogen-bonding behavior compared with unsubstituted phenylalanine. As a stepwise peptide-synthesis building block, the Boc protection supports controlled chemoselectivity of the amino functionality while the difluoro-substituted aromatic side chain provides a defined handle for preparing peptides and analogues used in structure-activity studies, protein engineering, and analytical method development.
CAT No: CP12904
Boc-2,6-Difluoro-L-Phenylalanine is a Boc-protected, stereodefined phenylalanine derivative featuring two fluorine atoms on the aromatic ring at the 2 and 6 positions. This combination of an N-protecting group and a fluorinated side-chain makes it a practical building block for assembling modified peptides and for medicinal chemistry programs that require aryl fluorination to tune physicochemical properties and metabolic stability profiles. In peptide and SAR workflows, the fluorinated aromatic ring provides a distinct handle for structure-activity relationship studies while the protected amino acid format supports controlled coupling during fragment synthesis.
1. Fluorinated Peptide Synthesis
Boc-2,6-Difluoro-L-Phenylalanine is used as a protected amino acid building block for custom peptide synthesis where incorporation of a difluorinated phenylalanine residue is required. Peptide chemists and peptide manufacturing groups select this reagent to introduce an electronically modified aromatic side chain while maintaining a protected amino terminus for stepwise assembly. The 2,6-difluoro substitution pattern is particularly valuable when researchers want to probe how steric and electronic effects from ortho-fluorination influence peptide conformation, binding interfaces, or structure-dependent properties in peptide libraries.
2. Medicinal Chemistry SAR Building Block
Boc-2,6-Difluoro-L-Phenylalanine is frequently incorporated into peptidomimetic scaffolds and medicinal chemistry intermediates to support structure-activity relationship (SAR) studies. Medicinal chemistry teams use the difluorinated phenylalanine motif to generate analog series in which aromatic electronics and lipophilicity-related parameters are systematically varied, while the Boc-protected amino functionality supports downstream derivatization into amide-containing fragments. This reagent is also used to prepare defined, stereochemically consistent intermediates for subsequent coupling steps in lead optimization workflows.
3. Pharmaceutical Intermediate Development
Boc-2,6-Difluoro-L-Phenylalanine serves as a stable, well-defined intermediate for manufacturing routes that require a fluorinated amino acid synthon. Process and development chemists use it to build amide and peptide-like linkages in the preparation of advanced intermediates for small-molecule and peptide-based drug discovery programs. The Boc protection provides a controlled functional-group profile for sequential chemistry, while the 2,6-difluoro aromatic ring helps ensure that the final scaffold retains the intended fluorination pattern introduced at the building-block stage.
4. Peptide Library Analog Design
Boc-2,6-Difluoro-L-Phenylalanine is applied in parallel synthesis and analog design efforts aimed at generating peptide libraries with defined aromatic substitutions. Researchers developing libraries for screening and mechanistic studies rely on this reagent to introduce a consistent difluorophenylalanine residue across multiple sequences, enabling direct comparison of how the 2,6-fluoro pattern affects local structure and chemical behavior. The protected format supports reproducible incorporation during automated or manual peptide assembly workflows, helping maintain sequence fidelity when constructing residue-specific variants.
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