2,5-Dichloro-D-Phenylalanine is a non-natural halogenated phenylalanine derivative in which the phenyl side chain is substituted with two chlorine atoms at the 2- and 5-positions and the α-amino acid backbone is in the D stereochemical form as indicated by the name. The molecule contains a free α-amino group and a free carboxyl group along with a chlorinated aromatic side chain that increases hydrophobicity and provides a distinct electronic profile for structure-property studies. In peptide and amino-acid derivative synthesis, it is used as a building block for incorporating halogenated aromatic residues into peptides and for generating defined analogues for chemical biology, protein-structure probing, and analytical method development where controlled side-chain substitution is required.
CAT No: CP12202
2,5-Dichloro-D-Phenylalanine is a D-configured, non-proteinogenic halogenated phenylalanine derivative featuring two chlorine atoms on the aromatic ring, which strongly influences hydrophobicity and electronic properties relative to unsubstituted phenylalanine. This compound is commonly handled as a chiral amino acid building block for synthetic and medicinal chemistry workflows where aromatic substitution pattern and stereochemistry are used to tune structure-activity relationships. Its amino acid functionality makes it a practical intermediate for preparing defined analogs used in peptide and peptidomimetic research.
1. Peptidomimetic Building Blocks
2,5-Dichloro-D-Phenylalanine is used by medicinal chemistry and chemical biology teams to assemble peptidomimetic structures and constrained analogs where D-amino acid stereochemistry and ring chlorination are leveraged to modulate conformation and physicochemical behavior. The halogenated aromatic side chain provides a distinct substitution pattern that can be carried through into short peptides, peptide-mimicking scaffolds, and SAR libraries, enabling systematic evaluation of how aromatic electronics and hydrophobic surface area impact downstream structure-property relationships. In these workflows, the compound is typically incorporated as a defined amino acid unit during synthesis of analog series intended for binding studies, protease stability screening, or physicochemical profiling.
2. Structure-Activity Relationship Analog Synthesis
2,5-Dichloro-D-Phenylalanine supports SAR development programs that require precise control over aromatic substitution and stereochemistry across series of analogs. Research groups in small-molecule and peptide-drug discovery use this building block to generate analogs that differ specifically at the phenyl ring substitution level (2,5-dichloro pattern) while maintaining the D-configuration at the amino acid center, helping isolate the contribution of aromatic halogenation to observed structure-activity trends. The compound's defined chiral amino acid framework also makes it a convenient starting material for preparing standardized intermediates used in parallel synthesis campaigns and analytical method development for analog characterization.
3. Chiral Intermediate For Medicinal Chemistry
2,5-Dichloro-D-Phenylalanine is frequently selected as a chiral intermediate in pharmaceutical intermediate development where a halogenated D-phenylalanine motif is required for downstream coupling into larger fragments. Process and R&D chemists use it to build defined stereochemical content into advanced intermediates used for medicinal chemistry exploration, including synthesis of protected derivatives and coupling-ready forms that preserve the 2,5-dichloro aromatic pattern. This makes the material particularly useful when the aromatic substitution pattern is critical for achieving the desired chemical identity of a target intermediate used in iterative synthesis and scale-up planning.
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