2,3-Difluoro-D-Phenylalanine is a non-natural, fluorinated amino acid derivative featuring a D-phenylalanine backbone with two fluorine atoms substituted at the 2- and 3-positions of the side-chain aromatic ring relative to the alpha carbon. The molecule contains a free amino group and a free carboxyl group and bears a difluorinated phenyl side chain that alters steric and electronic properties compared with unsubstituted phenylalanine while maintaining the chiral center implied by the D designation. It is used in peptide and structure-activity studies as a chemically defined building block for incorporating fluorinated aromatic residues, as well as in analytical method development and chemical biology workflows where fluorine substitution supports probing of conformation, binding interactions, or labeling contrast.
CAT No: CP12602
2,3-Difluoro-D-Phenylalanine is a D-configured, non-proteinogenic phenylalanine analog bearing two fluorine atoms at the 2- and 3-positions of the aromatic ring. The difluoro substitution provides distinct electronic and steric properties compared with phenylalanine, making it a useful building block for structure-activity relationship studies and for designing fluorinated peptidomimetics. Its stereochemical purity supports consistent incorporation into synthetic peptide-like frameworks used in chemical biology and medicinal chemistry workflows.
1. Peptidomimetic SAR Building Blocks
2,3-Difluoro-D-Phenylalanine is used as a fluorinated amino acid building block for peptidomimetic and peptide analog synthesis where aromatic ring electronics are tuned to probe structure-activity relationships. Medicinal chemistry groups incorporate this D-amino acid into short, conformationally constrained peptide-like sequences to evaluate how ring fluorination affects physicochemical properties and downstream molecular recognition in target binding assays. The presence of two aryl fluorine atoms enables chemists to systematically vary hydrogen-bonding patterns and aromatic polarization while maintaining a phenylalanine-like side chain architecture, supporting rational analog series development.
2. Fluorinated Chemical Biology Probes
2,3-Difluoro-D-Phenylalanine supports chemical biology experiments that rely on fluorinated amino acid analogs to track incorporation or to modulate labeling behavior in peptide-based probes. Researchers use D-configured fluorinated residues to build probe peptides that can be used in binding and interaction studies, where the fluorinated aromatic ring helps differentiate probe variants and supports comparative readouts across analog libraries. In workflows that generate peptide tags for downstream detection by mass spectrometry or fluorine-aware analytical methods, the difluoro motif provides a chemically stable handle that can be leveraged during probe design and library screening.
3. Stereodefined Medicinal Chemistry Intermediates
2,3-Difluoro-D-Phenylalanine is frequently selected as a stereodefined intermediate for the preparation of fluorinated drug-discovery candidates and advanced peptide-like intermediates where D-amino acid incorporation is used to control stereochemical composition of the final scaffold. Pharmaceutical intermediate development teams use this compound to assemble analogs that require consistent stereochemistry at the α-carbon while introducing difluorinated aromatic functionality for property modulation. The fluorinated phenyl ring also offers a practical design element for iterative medicinal chemistry campaigns, enabling chemists to build and compare series that differ specifically in aromatic substitution patterns while keeping the backbone stereochemical framework constant.
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