2,3-Dichloro-D-Phenylalanine is a non-natural, halogenated phenylalanine derivative in which the phenylalanine backbone bears two chlorine substituents at the 2- and 3-positions of the aromatic ring and the amino acid is specified in the D stereochemical form. The molecule contains an amino group and a carboxyl group on the alpha-carbon framework, with the chlorinated phenyl side chain providing increased hydrophobicity and electron-withdrawing character that can influence peptide coupling and conformational preferences. As a stereochemically defined, structurally modified amino acid, it is used in peptide synthesis and structure-activity studies to introduce halogenated aromatic functionality, and it can serve as a substrate or reference material in analytical method development for distinguishing substituted phenylalanine analogues.
CAT No: CP12002
2,3-Dichloro-D-Phenylalanine is a D-configured, non-proteinogenic halogenated phenylalanine analog bearing two chloro substituents at the 2 and 3 positions of the aromatic ring. This dense halogenation pattern makes it a useful chiral building block for medicinal chemistry and structure-activity relationship studies where electronic and steric effects of aryl chlorination are intentionally introduced. In synthetic workflows, it is typically handled as a specialty amino acid intermediate that can be incorporated into peptide-like scaffolds or used to prepare halogenated aromatic derivatives for downstream SAR and assay development.
1. Medicinal Chemistry SAR Building Block
2,3-Dichloro-D-Phenylalanine is used by medicinal chemistry teams to introduce a stereodefined, halogen-rich aryl motif into small-molecule leads and peptidomimetic scaffolds. The D-configuration supports the preparation of enantiomerically defined analog series when stereochemical control is required for potency, selectivity, or off-target profiling studies. The 2,3-dichloro substitution pattern provides a chemically robust handle for tuning aromatic electronics and hydrophobic character, and it is commonly selected when researchers want to compare how aryl halogenation impacts binding interactions in a structure-activity relationship (SAR) program.
2. Peptidomimetic And Analog Synthesis
2,3-Dichloro-D-Phenylalanine serves as a specialty amino acid building block for constructing peptide-like intermediates and constrained analogs used in chemical biology and drug discovery research. Its amino acid framework enables incorporation into amide-containing structures, including side-chain-modified fragments intended to mimic key spatial features of natural amino acid residues. The halogenated aromatic ring is particularly valuable in analog synthesis where researchers aim to modulate conformational preferences and physicochemical properties (such as lipophilicity and metabolic stability trends) through controlled aryl substitution, while maintaining a defined stereochemical center.
3. Chiral Intermediate For Halogenated Derivatives
2,3-Dichloro-D-Phenylalanine is frequently employed as a chiral intermediate for the preparation of further halogenated aromatic derivatives used in lead optimization and process development. Organic synthesis groups value the defined D-stereochemistry when building enantiopure libraries or when downstream steps require consistent stereochemical identity across batches. The two chloro substituents support systematic derivatization strategies, allowing chemists to access closely related aryl variants for comparative evaluation in screening follow-up campaigns, analytical method development, and reference material generation for structure confirmation workflows.
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