2,3-Dichloro-L-Phenylalanine is a halogenated, nonstandard amino acid derivative in which the phenylalanine side chain bears two chlorine substituents at the 2- and 3-positions relative to the benzylic carbon. The molecule contains a free amino group and a free carboxyl group characteristic of amino acids, with the L stereochemical configuration specified in the name, and it presents a substituted aromatic side chain that can modulate hydrophobicity and electronic properties through the chloro substituents. In peptide chemistry and chemical biology research, it is used as a defined building block for incorporating a dichloro-substituted phenylalanine residue into peptides or peptide analogues to support structure-activity studies, binding-site probing, and analytical method development where halogenated aromatic functionality provides a distinct chemical handle.
CAT No: CP12001
2,3-Dichloro-L-Phenylalanine is a halogenated, non-proteinogenic amino acid building block featuring two chlorine atoms on the aromatic ring and an L-stereocenter at the alpha position. The electron-withdrawing dichloro substitution makes it a useful structural handle for medicinal chemistry and peptide/peptidomimetic design where aromatic electronics and steric profile influence binding and reactivity. As a defined chiral amino acid derivative, it is commonly used as a specialty intermediate for preparing halogen-rich analogs and as an incorporation unit in synthetic peptide chemistry to probe structure-activity relationships.
1. Peptidomimetic SAR Building Block
2,3-Dichloro-L-Phenylalanine is used by medicinal chemistry and chemical biology groups to introduce a dichloro-substituted phenyl motif into peptidomimetics and constrained analogs during structure-activity relationship (SAR) studies. The double chlorination provides a distinct physicochemical signature on the aromatic ring, supporting systematic variation of aromatic electronics and hydrophobic/halogen-bonding character across analog series. Researchers often select this amino acid building block when they need a chiral, amino-acid-derived fragment that can be assembled into amide-rich scaffolds for downstream biological evaluation and comparative profiling in hit-to-lead optimization workflows.
2. Halogenated Peptide Synthesis
2,3-Dichloro-L-Phenylalanine serves as a specialty residue for custom peptide synthesis where a halogenated aromatic side chain is required for mechanistic studies, binding-site mapping, or analog generation. Peptide chemists incorporate this L-configured amino acid into sequences to create defined halogen-bearing peptides that can be used as reference materials in assay development, structure-function experiments, or comparative studies of aromatic substitution patterns. The dichloro substitution also helps generate peptides with improved chemical distinctness for analytical tracking (e.g., LC-MS method development and fragment-based characterization) relative to unsubstituted phenylalanine analogs.
3. Pharmaceutical Intermediate Development
2,3-Dichloro-L-Phenylalanine is widely used in pharmaceutical intermediate development as a chiral, halogenated amino acid precursor for preparing aromatic dichloro-containing fragments used in medicinal chemistry programs. Process and development chemists value this building block because it provides a direct route to incorporate the 2,3-dichlorophenyl motif into downstream heterocycles, amide linkers, and other drug-like scaffolds while maintaining stereochemical integrity at the alpha carbon. This makes it a practical choice for generating analog libraries and for producing well-defined intermediates used in scale-up-oriented synthesis planning.
4. Analytical Reference Material Preparation
2,3-Dichloro-L-Phenylalanine is also employed for analytical standard preparation and method development in laboratories working with halogenated amino acid derivatives and peptide-like compounds. Because the compound contains a clearly defined dichloro-substituted aromatic side chain and a chiral alpha-amino acid framework, it can be used to support identification, retention-time alignment, and mass spectral confirmation for related synthetic intermediates and final products. Analytical teams commonly include such stereochemically defined standards when building robust LC-MS workflows for monitoring synthesis progress, impurity profiling, and characterization of dichloro-phenylalanine-containing targets.
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