4-Chloro-D-Phenylalanine is a non-natural, D-configured phenylalanine derivative bearing a para-chloro substituent on the aromatic side chain, classifying it as a halogenated amino acid. The molecule contains a free amino group and a free carboxyl group on the alpha-carbon, with the side chain featuring a chlorinated benzyl aromatic ring that can influence polarity, hydrophobicity, and electronic properties relative to unmodified phenylalanine. It is used in peptide and structure-activity studies where incorporation of a halogenated phenylalanine analogue provides a defined chemical handle for conformational and binding investigations, as well as for analytical method development involving halogenated amino acid standards.
CAT No: CP11602
CAS No:14091-08-8
Synonyms/Alias:4-Chloro-D-phenylalanine;14091-08-8;(R)-2-AMINO-3-(4-CHLOROPHENYL)PROPANOICACID;(2R)-2-amino-3-(4-chlorophenyl)propanoicacid;D-4-Chlorophenylalanine;D-PCPA;D-PCP;D-4-CHLOROPHE;D-PHE(4-CL)-OH;147065-05-2;(R)-4-ChlorophenylalanineHydrochloride;(R)-4-ChlorophenylalanineHydrochlorideSalt;MFCD00079675;d-p-chlorophenylalanine;Tocris-0938;AC1LDI2L;Lopac-C-6506;H-D-4CPA-OH;D-4-CL-PHE;D-Phenylalanine,4-chloro-;H-P-CHLORO-D-PHE-OH;ZINC290;C9419_SIGMA;D-PHE(4-CL);SCHEMBL245828
4-Chloro-D-Phenylalanine is a D-configured phenylalanine analog bearing a para-chloro substituent on the aromatic ring, making it a stereochemically defined non-proteinogenic amino acid building block for peptide and peptidomimetic design. Its aryl chloride functionality provides a chemically distinctive handle for downstream derivatization and for generating analogs used in structure-activity relationship studies and chemical biology workflows where stereochemical control is essential. Researchers also use this compound as a defined chiral reference material and intermediate precursor when aromatic halogenation patterns are required for medicinal chemistry programs.
1. Peptidomimetic Building Blocks
4-Chloro-D-Phenylalanine is used by peptide chemistry groups to introduce a D-amino acid residue with a para-chloro aromatic side chain into peptidomimetics and modified peptide scaffolds. This stereodefined building block supports the preparation of analog series where aromatic substitution and D-configuration are systematically varied to probe structure-activity relationships, conformational preferences, and sequence-dependent behavior in synthetic peptide libraries. In custom peptide synthesis and medicinal chemistry development, the compound is selected when an aryl halogen pattern is needed to tune physicochemical properties or to enable later functional diversification of the side chain.
2. Medicinal Chemistry SAR Studies
4-Chloro-D-Phenylalanine is a practical reagent for medicinal chemistry teams developing halogenated amino acid analogs for SAR campaigns. The para-chloro substituent provides a distinct substitution motif that can influence electronic and steric characteristics of the aromatic side chain, while the D-configuration allows comparison against L-analog series in structure-activity mapping. Synthetic chemistry and chemical biology laboratories commonly incorporate this amino acid into short peptide-like fragments, peptidomimetic linkers, or constrained analogs to generate well-defined compounds for downstream screening workflows and physicochemical characterization.
3. Chemical Biology Probe Precursors
4-Chloro-D-Phenylalanine is used as a defined chiral precursor in chemical biology projects that require aromatic halogen functionality to support subsequent derivatization strategies. Researchers employ this building block when they need a stereochemically controlled residue to be carried through probe construction, affinity reagent synthesis, or labeling workflows that depend on maintaining the D-configuration and a specific aryl substitution pattern. The compound's non-proteinogenic nature also makes it useful for designing synthetic systems where incorporation is controlled by chemical synthesis rather than biological translation.
4. Chiral Reference and Standards
4-Chloro-D-Phenylalanine is also used in analytical chemistry settings as a defined chiral amino acid analog for method development and reference standard preparation. Laboratories use it to support LC-MS or related analytical workflows that require an unambiguous mass and stereochemical identity for quantitation, identity confirmation, or impurity profiling in synthetic intermediate streams. Because the compound is structurally specific (D-configuration and para-chloro substitution), it is particularly useful when analytical methods must distinguish closely related phenylalanine analogs or halogenated variants.
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