Cbz-2,6-Dichloro-D-Phenylalanine is a protected, non-natural amino acid derivative in which the phenylalanine backbone bears two chlorine substituents at the 2 and 6 positions of the aromatic ring and is present in the D stereochemical form as indicated by the product name. The molecule contains an N-terminal Cbz (benzyloxycarbonyl) protecting group that masks the amino functionality and a free carboxyl group, while the side chain features a substituted benzyl/phenyl group with electron-withdrawing halogens that modulate aromatic hydrophobicity and steric environment. As a Cbz-protected amino acid, it is used as a building block for peptide and peptidomimetic synthesis and for structure-activity or chemical biology studies where halogenated, D-configured aromatic amino acid residues are incorporated or used as defined analytical standards.
CAT No: CP12309
Cbz-2,6-Dichloro-D-Phenylalanine is a D-configured phenylalanine derivative bearing a benzyloxycarbonyl (Cbz) protecting group on the α-amino function and two chlorine substituents at the 2- and 6-positions of the aromatic ring. The molecule combines a stereogenic α-carbon with an aryl side chain that is electronically deactivated and sterically hindered by ortho chlorination, which can influence coupling rates and subsequent electrophilic aromatic transformations. The Cbz carbamate is stable under many peptide-coupling conditions yet can be removed under hydrogenolysis or strong hydrogenation-compatible workflows to reveal the free amino group for iterative peptide assembly. The presence of the dichloro aryl motif also makes the compound a practical chiral intermediate for downstream aryl functionalization, including nucleophilic aromatic substitution and cross-coupling strategies that preserve the amino acid stereochemistry.
1. Peptide Synthesis
Cbz-2,6-Dichloro-D-Phenylalanine supports protected amino acid synthesis and peptide building block preparation where a Cbz-protected D-phenylalanine residue is required. The α-Cbz carbamate provides an orthogonal amine protection handle for standard amide bond formation at the carboxyl group while maintaining the D-configuration at the stereocenter during coupling. The 2,6-dichloro substitution on the phenyl side chain can be used to tune hydrophobicity and aromatic reactivity in peptide analogs, enabling controlled incorporation of sterically encumbered aryl surfaces. Peptide fragments prepared from this residue can serve as substrates for subsequent side-chain derivatization or as defined stereochemical probes in peptide science and chemical biology workflows.
2. Peptidomimetics And SAR Studies
Cbz-2,6-Dichloro-D-Phenylalanine is suitable for peptidomimetic construction and structure-activity relationship studies that require a D-amino acid with a halogenated aromatic pharmacophore. The protected α-amino group and carboxyl functionality enable systematic replacement of natural L-phenylalanine positions with a stereochemically defined D-analog during library synthesis. The 2,6-dichloro pattern can modulate conformational preferences and electronic distribution of the aromatic ring, which may affect binding pocket interactions in SAR-focused analog series. Downstream diversification through aryl cross-coupling or nucleophilic substitution can generate a range of substituted phenylalanine mimics while retaining the original amino acid backbone stereochemistry.
3. Side-Chain Functionalization
Cbz-2,6-Dichloro-D-Phenylalanine can be employed as a chiral aryl-intermediate for side-chain functionalization strategies in synthetic organic chemistry. The dichloro aromatic ring functions as a reactive platform for transformation into alternative substituents via cross-coupling chemistry or nucleophilic aromatic substitution, while the Cbz-protected amino group helps prevent undesired amine participation during aryl modification steps. The D-configuration at the α-carbon provides stereochemical continuity from the initial amino acid building block into the final functionalized derivative. Resulting products can include halogen-to-heteroatom substituted aryl analogs, aryl-conjugated motifs, or further elaborated peptidomimetic fragments used in medicinal chemistry research and applied scaffold generation.
4. Chemical Biology Probes
Cbz-2,6-D-Phenylalanine is applicable to chemical biology research where defined stereochemistry and modifiable aromatic side chains support molecular recognition studies. The Cbz-protected amine enables incorporation into peptide-like constructs that can later be deprotected to generate a reactive amino handle for conjugation or further derivatization. The sterically congested 2,6-dichloro phenyl group can serve as a stable aromatic element that resists certain electrophilic side reactions while remaining compatible with post-assembly aryl functionalization routes. Constructed probes derived from this residue can be used to interrogate binding interactions, evaluate stereochemical effects of D-amino acid incorporation, and generate well-defined intermediates for downstream biomolecule modification.
5. Pharmaceutical Intermediate Preparation
Cbz-2,6-Dichloro-D-Phenylalanine is suitable for pharmaceutical intermediate preparation in fine chemical synthesis workflows that require protected D-amino acid building blocks. The Cbz carbamate protects the α-amino group to support controlled peptide coupling chemistry or conversion into activated derivatives for further synthetic steps, while the carboxyl functionality enables transformation into amide-forming intermediates. The dichloro aromatic side chain provides a handle for later medicinal chemistry diversification, including formation of substituted aromatic rings that can be carried through toward drug-like candidates or process-specific analogs. The compound's stereochemical integrity and protecting-group stability make it compatible with manufacturing-oriented route design where chiral amino acid intermediates must be handled reproducibly across multi-step sequences.
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