2,6-Dichloro-D-Phenylalanine is a halogenated, non-natural amino acid derivative featuring a D-configuration at the α-carbon and a phenylalanine backbone bearing two chlorine substituents at the 2- and 6-positions of the aromatic ring. The molecule contains both an amino group and a carboxyl group, with the side chain presenting a di-chlorinated benzyl aromatic functionality that can modulate hydrophobicity and electronic properties relative to unsubstituted phenylalanine. It is used in peptide and amino acid chemistry for structure-activity studies, incorporation into synthetic peptides to probe steric and electronic effects of ring substitution, and as a defined building block for analytical method development and chemical biology labeling strategies where a halogenated aromatic handle is required.
CAT No: CP12302
2,6-Dichloro-D-Phenylalanine is a D-configured, non-proteinogenic phenylalanine analog bearing two chlorine substituents at the 2 and 6 positions of the aromatic ring. This sterically hindered, halogenated side chain makes it a useful building block for medicinal chemistry and peptide/peptidomimetic design where aromatic substitution pattern and conformational/steric effects are deliberately tuned. In research settings, it is typically handled as a chiral amino acid building block for incorporation into defined sequences or for preparing halogen-rich intermediates used in structure-activity relationship (SAR) studies.
1. Peptidomimetic Building Block
2,6-Dichloro-D-Phenylalanine is used by medicinal chemistry and chemical biology groups to introduce a D-amino acid motif and a sterically encumbered, dichloro-substituted aromatic side chain into peptides and peptidomimetics. This supports the development of sequence-defined analogs for studying how aromatic halogenation and D-configuration influence conformation, physicochemical properties, and structure-activity relationships. The compound is commonly selected when researchers need a non-natural aromatic substitution pattern that can be carried through to downstream coupling workflows for custom peptide synthesis and analog libraries.
2. Medicinal Chemistry SAR Synthesis
2,6-Dichloro-D-Phenylalanine serves as a chiral amino acid intermediate for preparing halogenated fragments used in SAR campaigns, particularly where aromatic dichloro substitution is used to modulate lipophilicity, steric profile, and binding-site complementarity in small-molecule or peptide-like candidates. Pharmaceutical intermediate development teams rely on this building block to access D-configured, halogen-rich scaffolds that can be diversified into analog series with controlled stereochemistry. Its defined substitution pattern makes it a practical choice for route development where the aromatic ring substitution must remain unchanged across multiple synthetic steps.
3. Structure-Defined Peptide Analog Libraries
2,6-Dichloro-D-Phenylalanine is applied in research workflows that generate structure-defined peptide analog libraries, including D-amino acid-containing sequences used to probe sequence effects and aromatic side-chain contributions. Custom peptide synthesis groups incorporate this residue to create defined analogs for downstream biological or biophysical evaluation by collaborators, while keeping the aromatic dichloro pattern consistent across variants. The sterically substituted aromatic ring helps researchers systematically vary side-chain electronics and steric bulk while maintaining the same backbone stereochemical identity, which is valuable for comparative studies of analog series.
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