3,5-Dichloro-D-Phenylalanine is a non-proteinogenic, halogenated amino acid derivative featuring a D-phenylalanine backbone with two chlorine substituents at the 3 and 5 positions of the aromatic side chain. The molecule contains a free amino group and a carboxyl group, while its side chain bears a dichlorophenyl ring that increases hydrophobicity and provides distinct electronic properties compared with unsubstituted phenylalanine. As a stereodefined, structurally modified amino acid, it is used in peptide and structure-activity studies to probe how aromatic halogenation and D-configuration influence conformational preferences, binding interactions, and labeling or analytical behavior of amino acid-containing constructs.
CAT No: CP12502
3,5-Dichloro-D-Phenylalanine is a D-configured, non-proteinogenic phenylalanine analog bearing two chlorine substituents on the aromatic ring. This halogenated side chain increases hydrophobicity and aromatic electron density while maintaining the amino acid backbone required for downstream chemical handling. In research and development workflows, it is typically used as a defined chiral building block for constructing halogenated peptidomimetics, structure-activity relationship (SAR) analogs, and medicinal chemistry intermediates where stereochemistry and aromatic substitution pattern are critical.
1. Peptidomimetic Building Block
3,5-Dichloro-D-Phenylalanine is used by medicinal chemistry and chemical biology groups to prepare D-amino acid-containing peptides and peptidomimetics that probe how aromatic halogenation and stereochemistry influence conformation and target interactions. The 3,5-dichloro substitution pattern provides a clear, reproducible handle for SAR studies, while the D-configuration supports the synthesis of stereochemically defined analog series. Typical downstream work includes incorporation into short peptide-like scaffolds and derivatization into analogs used for binding studies, protease-stability comparisons, and conformational mapping in vitro.
2. SAR Analog Synthesis
3,5-Dichloro-D-Phenylalanine serves as a specialized aromatic substitution intermediate for generating halogenated analog libraries in lead optimization programs. Researchers use it to vary the electronic and steric profile of the phenylalanine side chain without changing the amino acid backbone identity, enabling controlled comparisons across analog sets. Its defined stereochemistry and substitution pattern make it particularly useful when downstream assays require consistent structural features, such as when synthesizing series of D-amino acid analogs for structure-activity relationship evaluation and mechanistic chemistry studies.
3. Pharmaceutical Intermediate Development
3,5-Dichloro-D-Phenylalanine is commonly selected as a chiral, halogenated amino acid building block during pharmaceutical intermediate development for routes that require precise aromatic substitution and D-stereochemical control. Process and development chemists incorporate this scaffold into larger synthetic sequences to access halogenated D-amino acid motifs used in drug-discovery programs and specialty chemical manufacturing. The product's stable, well-defined composition supports reproducible intermediate specification for custom synthesis, scale-up planning, and analytical confirmation during candidate-analog preparation.
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