Boc-2,6-Difluoro-D-Phenylalanine is a protected, non-natural amino acid derivative in which the amino group is masked as a Boc carbamate and the side chain is a substituted phenyl ring bearing two fluorine atoms at the 2 and 6 positions. The molecule contains a free carboxylic acid functionality and a stereodefined D-configuration at the alpha carbon, while the fluorinated aromatic ring modulates hydrophobicity and introduces strong electron-withdrawing character that can affect conformational preferences and intermolecular interactions in peptide contexts. As a Boc-protected amino acid, it is used as a building block for stepwise peptide synthesis and for structure-activity or chemical biology studies where incorporation of a difluorinated phenylalanine residue and its electronic effects are examined.
CAT No: CP12905
Boc-2,6-Difluoro-D-Phenylalanine is a D-configured, non-proteinogenic phenylalanine analog bearing two fluorine atoms at the 2 and 6 positions of the aromatic ring, supplied as an N-Boc protected amino acid building block. This combination of stereochemistry and sterically/ electronically modulated difluoro-substitution makes it a useful residue for structure-activity relationship studies and for preparing conformationally and physicochemically tuned peptide fragments. The Boc group supports standard protected-amino-acid workflows used in peptide synthesis and intermediate manufacturing.
1. Peptide Fragment Synthesis
Boc-2,6-Difluoro-D-Phenylalanine is used by peptide chemists to incorporate a difluoro-substituted, D-amino acid residue into protected peptide segments and final peptide constructs. The N-Boc protection enables routine coupling strategies in segment assembly workflows, while the 2,6-difluoro aromatic substitution provides a chemically robust handle for tuning aromatic electronics and steric environment around the side chain. Researchers commonly select this residue when they want to compare analogs that differ specifically at the aromatic ring substitution pattern, or when they aim to modulate properties such as local hydrophobicity and aromatic-backbone interactions in peptide libraries.
2. Peptidomimetic And SAR Studies
Boc-2,6-Difluoro-D-Phenylalanine supports medicinal chemistry programs focused on peptidomimetic development and systematic structure-activity relationship (SAR) work. The D-configuration and difluoro-phenyl side chain are frequently leveraged to generate analog series that probe how stereochemical inversion and aromatic fluorination influence compound behavior in chemical biology assays and downstream lead optimization. Because the fluorinated aromatic ring is a common motif for improving metabolic and physicochemical profiles in small-molecule design, this building block is often chosen to translate those design principles into peptide-like architectures during analog synthesis and comparative evaluation.
3. Pharmaceutical Intermediate Building Block
Boc-2,6-Difluoro-D-Phenylalanine is also employed as a chiral amino acid intermediate for the preparation of fluorinated, stereodefined fragments used in custom synthesis. Process and development chemists use this type of protected amino acid building block to access difluoro-aryl substituted chiral motifs that can be carried forward into larger intermediate sequences for peptide-derived candidates and specialty chemical targets. The N-Boc protection provides a practical staging form for controlled downstream functionalization, enabling consistent handling during multi-step manufacturing of research-grade intermediates and analog libraries.
4. Analytical Reference Standards
Boc-2,6-Difluoro-D-Phenylalanine is useful for analytical method development and reference material preparation in workflows that quantify or characterize difluoro-aryl amino acid residues and related peptide fragments. Analytical teams use such protected amino acid building blocks to generate authentic standards for LC-MS/HRMS identification, retention-time benchmarking, and impurity profiling during synthesis development. Its defined stereochemistry and distinct aromatic fluorination pattern make it a practical reference point when validating analytical methods for peptide analogs containing fluorinated D-phenylalanine motifs.
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