Boc-2,6-Dichloro-D-Phenylalanine is a protected, non-natural amino acid derivative featuring a D-phenylalanine backbone with two chlorine atoms at the 2- and 6-positions of the aromatic ring. The molecule contains a Boc-protected amino group and a free carboxyl group, while the dichloro-substituted phenyl side chain provides increased halogenation and altered hydrophobic and electronic character compared with unsubstituted phenylalanine. As a stepwise peptide-synthesis building block, the Boc protection supports chemoselective handling of the amino functionality and the modified aromatic ring serves as a structural handle for preparing halogenated peptide analogues used in structure-activity studies, chemical biology labeling, and analytical method development.
CAT No: CP12305
Boc-2,6-Dichloro-D-Phenylalanine is a Boc-protected D-amino acid building block bearing a 2,6-dichloro-substituted phenyl side chain, combining stereochemical control with a strongly electron-withdrawing, hydrophobic aromatic functionality. This protected form is commonly leveraged in peptide and peptidomimetic synthesis workflows where the D-configuration and halogenated aromatic residue are used to tune conformation, improve chemical robustness during assembly, and support structure-activity relationship studies. The Boc group provides a stable, acid-labile N-terminal protection strategy for downstream coupling steps in custom synthesis programs.
1. D-Amino Acid Peptide Building
Boc-2,6-Dichloro-D-Phenylalanine is used by peptide synthesis groups to introduce a D-configured, halogenated aromatic residue into short peptides, constrained segments, and peptidomimetic scaffolds. The 2,6-dichloro substitution increases side-chain hydrophobic character and steric bulk around the aromatic ring, which can be valuable when researchers aim to modulate local structure and physicochemical properties while assembling stereochemically defined sequences. In practice, this reagent is selected for segment coupling and library synthesis where maintaining the D-configuration through the protected intermediate stage is essential.
2. Peptidomimetic Structure-Activity Studies
Medicinal chemistry teams use Boc-2,6-Dichloro-D-Phenylalanine as a residue-level variable in SAR campaigns for peptide-like inhibitors, receptor ligands, and protease-targeting chemotypes. The dichloro-phenyl side chain provides a convenient handle for exploring how halogen substitution patterns influence potency-relevant properties such as hydrophobicity, aromatic packing, and conformational preferences within a designed backbone. Because the amino acid is already N-protected, it fits standard protected amino acid building block workflows used to rapidly generate analog series for downstream biological testing and formulation screening.
3. Pharmaceutical Intermediate Synthesis
Boc-2,6-Dichloro-D-Phenylalanine is also used as a chiral, protected amino acid intermediate in the development of halogenated aromatic amino acid derivatives for process chemistry and specialty chemical manufacturing. The combination of D-stereochemistry and Boc protection supports reliable downstream functional transformations in multi-step intermediate routes, including conversion to activated derivatives for further coupling or incorporation into more complex scaffolds. Industrial and contract research organizations often select this type of building block when a defined stereochemical center and a protected amine are required to control impurity profiles and reproducibility across synthetic batches.
4. Protected Residue Library Production
Boc-2,6-Dichloro-D-Phenylalanine supports peptide and peptidomimetic library production where researchers need a consistent, protected residue for parallel synthesis of sequence variants. The Boc-protected format aligns with common protected-amino-acid handling practices for automated or semi-automated assembly, enabling controlled incorporation of the 2,6-dichloro-D-phenylalanine motif into multiple analogs. This makes it a practical choice for screening-focused chemistry teams that require residue-level interchangeability while keeping the stereochemical and protection-state attributes uniform across a compound set.
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