Boc-2,3-Dichloro-D-Phenylalanine is a Boc-protected, nonstandard amino acid derivative in which the phenylalanine backbone bears two chloro substituents at the 2- and 3-positions of the aromatic ring and is presented in the D stereochemical form as indicated by the product name. The molecule contains a Boc-protected amino group and a free carboxyl functional group, while the chlorinated phenyl side chain provides a halogenated aromatic functionality that can influence hydrophobicity and electronic character during peptide assembly or structure-activity studies. In synthesis, this protected analogue is used as a building block for incorporating a halogenated phenylalanine residue into peptides or peptide-related intermediates, supporting chemoselective stepwise coupling while the Boc group helps prevent undesired reactions at the amine.
CAT No: CP12005
Boc-2,3-Dichloro-D-Phenylalanine is a D-configured, non-proteinogenic amino acid building block bearing two vicinal chloro substituents on the alpha-carbon framework and a Boc-protected amino group. The benzylic phenyl side chain combined with the 2,3-dichloro substitution pattern makes this scaffold valuable for stereodefined peptide and peptidomimetic synthesis where halogenated amino acid residues are used to probe structure-activity relationships, conformational effects, and chemical reactivity. As a Boc-protected intermediate, it is commonly handled as an amino acid derivative for downstream coupling into protected peptide segments and for preparation of medicinal chemistry intermediates.
1. Peptidomimetic Building Blocks
Boc-2,3-Dichloro-D-Phenylalanine is used by medicinal chemistry and peptide chemistry groups to assemble halogenated peptidomimetic sequences that incorporate sterically and electronically distinct residues. The D-stereochemistry and the 2,3-dichloro substitution pattern support SAR workflows where researchers compare analogs that vary halogenation and stereochemical configuration while keeping the rest of the scaffold constant. In custom peptide synthesis and research library construction, the Boc-protected amino functionality enables controlled segment coupling into protected peptide intermediates, supporting the preparation of defined, residue-specific analogs for downstream biological or physicochemical characterization.
2. Structure-Activity Relationship Studies
Boc-2,3-Dichloro-D-Phenylalanine is a practical choice for SAR studies in small-molecule and peptide-drug discovery programs aiming to quantify how alpha-substitution halogens influence molecular shape, polarity, and chemical stability trends across analog series. Organic and medicinal chemistry teams frequently incorporate such halogenated amino acid residues into constrained or modified backbones to generate structure-defined variants for comparative profiling. The presence of two chloro substituents provides a clear "handle" for systematic variation in steric bulk and inductive effects, while the protected amino group supports integration into multi-step analog synthesis routes where amine protection is required for selective transformations.
3. Pharmaceutical Intermediate Development
Boc-2,3-Dichloro-D-Phenylalanine is also used as a chiral amino acid intermediate for preparing advanced pharmaceutical intermediates and specialized building blocks for process chemistry development. Process and synthetic chemistry teams select this type of protected, stereodefined halogenated amino acid derivative when the downstream route requires a stable, isolable intermediate that preserves stereochemical integrity and the halogenated motif through key synthetic steps. The Boc protection supports compatibility with protected-intermediate workflows, allowing the residue to be carried forward into further functionalization or coupling steps used to generate final research compounds and analog sets.
4. Halogenated Residue Libraries
Boc-2,3-Dichloro-D-Phenylalanine is employed in the creation of residue-focused libraries where researchers need consistent incorporation of a halogenated D-phenylalanine motif across multiple peptide-like constructs. Chemical biology and peptide engineering teams use such building blocks to generate panels of analogs for screening of backbone-modified architectures, including sequences designed to test how halogen placement correlates with downstream reactivity or physicochemical behavior. Because the reagent is already protected at the amino terminus, it fits established protected-segment assembly workflows used to produce multiple defined constructs with minimized variability in residue handling.
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