3,4-Dichloro-D-Phenylalanine is a halogenated, non-natural amino acid derivative in the phenylalanine family, featuring a benzyl side chain bearing two chlorine substituents at the 3 and 4 positions relative to the benzylic carbon. The molecule contains a free amino group and a free carboxyl group and is specified as the D stereochemical form, with the dichloro substitution imparting increased hydrophobicity and altered electronic character on the aromatic side chain compared with unsubstituted phenylalanine. In research and synthesis, it is used as a substrate analog for structure-activity and binding studies, as a building block for incorporating halogenated aromatic residues into peptides, and as a chemically distinct amino acid for analytical method development and molecular labeling workflows.
CAT No: CP12402
CAS No:52794-98-6
Synonyms/Alias:52794-98-6;(R)-2-Amino-3-(3,4-dichlorophenyl)propanoicacid;D-3,4-Dichlorophenylalanine;3,4-Dichloro-D-Phenylalanine;(2R)-2-amino-3-(3,4-dichlorophenyl)propanoicacid;D-3,4-DICHLOROPHE;H-D-Phe(3,4-DiCl)-OH;H-3,4-DICHLORO-D-PHE-OH;DICHLOROPHE;AmbotzHAA6380;PubChem18703;AC1ODU3C;D-3,4-Dichlorophenlalanine;SCHEMBL289165;D-3,4-Dichloro-phenylalanine;3,4-DICHLORO-D-PHE-OH;D-PHE(3,4-DICL)-OH;MolPort-001-758-767;H-D-PHE(3,4-CL2)-OH;ZINC1653227;MFCD00671682;3,4-DICHLOROPHENYL-D-ALANINE;AB06767;AC-5851;AM82041
3,4-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 provides a rigid, electronically modified aromatic environment that is frequently leveraged in peptide drug discovery, peptidomimetic design, and structure-activity relationship studies. As a chiral amino acid building block, it is commonly used to introduce steric and electronic effects at a defined position within synthetic peptides and small-molecule scaffolds.
1. Peptidomimetic Building Blocks
3,4-Dichloro-D-Phenylalanine is used by medicinal chemistry and peptide chemistry groups to incorporate a halogenated D-amino acid residue into peptidomimetics and constrained peptide analogs. The D-stereochemistry and 3,4-dichloro-substituted aromatic side chain enable researchers to probe how backbone configuration and aromatic electronics/sterics influence key properties such as conformation and structure-activity relationships. In practice, it is selected when a developer wants a non-proteinogenic residue that can be installed at a specific position during custom peptide synthesis to generate analog panels for SAR screening and lead optimization.
2. Protease Resistance Studies
3,4-Dichloro-D-Phenylalanine is frequently employed in chemical biology workflows that assess how non-natural amino acid substitution affects peptide stability in protease challenge experiments. The combination of D-configuration and the bulky, electron-withdrawing dichloro aromatic ring provides a chemically defined modification that researchers can place within peptide sequences to evaluate degradation patterns and compare analogs. This makes the reagent valuable for designing stability-focused peptide libraries used in preclinical research settings, where relative susceptibility to enzymatic cleavage is monitored across a series of site-specific substitutions.
3. SAR and Binding Probe Design
3,4-Dichloro-D-Phenylalanine supports structure-activity relationship studies where aromatic substitution patterns are systematically varied to map the contribution of ring substitution to binding and recognition motifs. By using this specific 3,4-dichloro-D-phenylalanine building block, researchers can generate analogs that differ primarily in side-chain electronics and steric profile while keeping the rest of the scaffold constant. Such analog panels are also used to construct chemical biology probes and reference peptides for mechanistic experiments, where controlled incorporation of a halogenated D-amino acid helps distinguish the role of aromatic environment in receptor/ligand interactions.
4. Chiral Intermediate Development
3,4-Dichloro-D-Phenylalanine is used as a chiral amino acid intermediate in downstream synthetic programs that require a defined D-amino acid stereocenter and a halogenated aromatic handle for further functionalization. Pharmaceutical intermediate teams and specialty chemical manufacturers incorporate this building block into larger synthetic sequences to access halogenated aromatic amino acid derivatives, peptide coupling partners, or scaffold fragments used in medicinal chemistry campaigns. The presence of two chlorine substituents also makes the molecule a practical starting point for generating derivative series where aromatic substitution is retained as a structural feature across multiple candidate compounds.
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