3-Chloro-D-Phenylalanine is a non-natural, D-configured amino acid derivative featuring a chlorinated phenyl side chain attached to the α-amino and α-carboxyl groups. The molecule bears a 3-chloro substituent on the aromatic ring, with the amino group and carboxylic acid functionality providing handles for salt formation and peptide-bond construction while the halogenated aromatic side chain modulates polarity and steric/electronic character relative to unsubstituted phenylalanine. In peptide chemistry and chemical biology, it is used as a building block to introduce a halogen-bearing aromatic residue for structure-activity studies, conformational probing, and analytical labeling where the presence of the chloro substituent can support downstream derivatization or detection strategies.
CAT No: CP11502
CAS No:80126-52-9
Synonyms/Alias:80126-52-9;3-Chloro-D-phenylalanine;(R)-2-AMINO-3-(3-CHLOROPHENYL)PROPANOICACID;H-D-Phe(3-Cl)-OH;D-PHE(3-CL)-OH;D-3-CHLOROPHE;D-3-Chlorophenylalanine;(2R)-2-amino-3-(3-chlorophenyl)propanoicacid;PubChem11977;3-CHLORO-D-PHE-OH;D-3-CL-PHE;SCHEMBL298829;M-CHLORO-D-PHENYLALANINE;CTK3J1806;(R)-3-CHLOROPHENYLALANINE;MolPort-001-758-732;ZINC2382502;AKOS017482258;AB09412;AC-5842;AM82742;FS-2458;RTR-025395;AJ-34866;AK162592
3-Chloro-D-Phenylalanine is a D-configured, non-proteinogenic phenylalanine analog bearing a chloro substituent on the aromatic ring. This aryl-chloride functionality makes it a useful electrophile handle for downstream derivatization, while the D-stereochemistry supports incorporation into stereochemically defined peptide and peptidomimetic structures. In chemical biology and medicinal chemistry workflows, it is commonly selected as a halogenated amino acid building block to probe structure-property relationships and to introduce site-specific aromatic substitution patterns into synthetic targets.
1. Peptidomimetic Building Blocks
3-Chloro-D-Phenylalanine is widely used in the preparation of D-amino acid-containing peptides, peptidomimetics, and constrained analogs where stereochemical control is required. Medicinal chemistry groups and custom peptide synthesis providers use this halogenated phenylalanine building block to introduce a chlorinated aromatic side chain that can influence conformational preferences and physicochemical properties of the resulting sequence. Because the molecule is an amino acid derivative with a defined D configuration, it supports the assembly of stereochemically consistent libraries for structure-activity relationship studies and for generating analog series where the aromatic substitution pattern is varied systematically.
2. Medicinal Chemistry SAR Intermediates
3-Chloro-D-Phenylalanine serves as a practical intermediate for medicinal chemistry programs that require a chlorinated aromatic amino acid motif for analog synthesis. Researchers use it to access D-configured, aryl-chloride-containing scaffolds that can be further functionalized in later synthetic steps to generate substituted aromatic variants. The aryl chloride is particularly valuable when downstream diversification is needed to tune electronic and steric features of the aromatic ring, enabling efficient SAR workflows in small-molecule and peptide-like drug discovery chemistry.
3. Chemical Biology Probe Synthesis
3-Chloro-D-Phenylalanine is used in chemical biology for constructing labeled or reactive peptide/probe scaffolds that rely on a chlorinated aromatic handle for subsequent conjugation or derivatization. Probe development teams employ this building block to embed a defined D-amino acid stereocenter and a chlorinated phenyl side chain into synthetic ligands, affinity reagents, or mechanistic probes. The resulting chlorinated aromatic motif can be leveraged during later functionalization steps to attach tags, reporters, or binding elements while maintaining a controlled stereochemical framework within the probe structure.
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