Cbz-2,4-Dichloro-D-Phenylalanine is a Cbz-protected, non-natural amino acid derivative featuring a D-configuration at the α-carbon and a 2,4-dichloro-substituted phenyl side chain, classifying it as a halogenated phenylalanine analogue. The molecule contains a carbobenzyloxy (Cbz) protecting group on the amino functionality, while the carboxyl group remains available for peptide-coupling chemistry and the dichloro aromatic ring provides increased hydrophobicity and electron-withdrawing character relative to unsubstituted phenylalanine. In synthesis, this protected amino acid is used as a building block for preparing modified peptides and structure-activity studies where the presence of the 2,4-dichloro phenyl motif and the D-stereocenter are used to probe conformational and physicochemical effects.
CAT No: CP12109
Cbz-2,4-Dichloro-D-Phenylalanine is a D-configured phenylalanine derivative bearing two chlorine substituents on the aromatic ring at the 2- and 4-positions, which modulate hydrophobicity and electrophilic aromatic reactivity. The α-amino group is carbamate-protected as a benzyloxycarbonyl (Cbz) group, while the side chain remains an unmodified benzyl moiety consistent with phenylalanine-based peptide chemistry. The molecule contains a single stereogenic center at the α-carbon, enabling stereochemically defined incorporation into peptide sequences or as a chiral intermediate for amino acid derivatization. The aromatic dichloro pattern can participate in downstream functionalization and serves as a stable, nonpolar handle for structure-guided molecular design and synthetic intermediate preparation.
1. Protected Amino Acid Synthesis
Cbz-2,4-Dichloro-D-Phenylalanine is employed in protected amino acid synthesis workflows where carbamate protection supports controlled N-functionalization during peptide building block preparation. The Cbz-protected α-amine and the D-stereocenter allow compatibility with standard peptide coupling strategies after orthogonal deprotection, while the 2,4-dichlorophenyl side chain provides a defined hydrophobic/aromatic motif for subsequent structure-activity relationship studies. The dichloro substitution pattern can be retained through peptide assembly, enabling downstream transformations that depend on the aromatic substitution pattern rather than on the backbone functionality. The resulting chiral, N-protected amino acid derivative can be used to generate D-amino acid containing fragments for synthetic organic chemistry and biochemical research intermediate preparation.
2. Peptide Synthesis
Cbz-2,4-Dichloro-D-Phenylalanine is suitable for peptide synthesis and peptidomimetic construction where a protected D-phenylalanine residue is required to control stereochemistry at the α-position. The Cbz carbamate functions as an N-protection strategy that can be removed under orthogonal conditions to reveal the reactive amine for sequential coupling steps, while the aromatic dichloro side chain remains chemically stable under typical peptide assembly conditions. The D-configuration supports incorporation into peptides designed to resist proteolysis and to probe stereochemical effects on folding and binding, with the 2,4-dichlorophenyl group providing a rigid, halogenated aromatic interaction surface. The compound therefore functions as a defined residue for assembling D-amino acid peptides and related analogs used in mechanistic studies and molecular scaffold development.
3. SAR And Molecular Design
Cbz-2,4-Dichloro-D-Phenylalanine is applied in SAR studies and fragment-based molecular design where the halogenated aromatic side chain enables systematic variation of lipophilicity, steric profile, and aryl interaction geometry. The D-phenylalanine backbone provides stereochemical control that can be used to compare D- versus L-analog behavior in structure-guided synthesis, while the Cbz-protected amine supports incorporation into larger scaffolds without premature side reactions. The 2,4-dichloro substitution pattern can serve as a persistent pharmacophore-like element in peptide analogs, allowing subsequent derivatization routes to focus on backbone elaboration rather than on aromatic reconfiguration. The compound can be used to prepare analog series for biochemical research intermediate generation and to support iterative design cycles in applied medicinal chemistry.
4. Bioconjugation Chemistry
Cbz-2,4-Dichloro-D-Phenylalanine can be used in bioconjugation chemistry to introduce a defined D-amino acid motif into peptide-based linkers, affinity reagents, or labeling handles. The Cbz-protected α-amine enables controlled deprotection to generate a coupling-ready amine for attachment strategies that build conjugates through amide formation or related bond-forming steps. The halogenated aromatic side chain can act as a hydrophobic anchor that influences conjugate solubility and binding to hydrophobic pockets in biomolecular targets or to polymeric matrices used in labeling workflows. The compound's stereodefined D-configuration supports the construction of stable conjugates and peptide-derived materials where stereochemistry affects recognition and stability in biochemical research.
5. Process Chemistry Intermediate
Cbz-2,4-Dichloro-D-Phenylalanine is relevant to process chemistry intermediate preparation for manufacturing routes that require a chiral, N-protected amino acid with a robust aromatic substituent pattern. The Cbz protecting group provides a predictable handle for orthogonal deprotection and subsequent coupling operations, supporting scalable synthesis of D-amino acid derivatives and peptide building blocks. The dichlorophenyl side chain can be carried through synthetic sequences as a stable structural element, reducing the need for late-stage aromatic installation and enabling route design that separates backbone assembly from final functional tuning. The compound can therefore serve as a defined intermediate for fine chemical synthesis and specialty chemical production where stereochemical fidelity and protected-group compatibility are central to downstream manufacturing of amino acid derivatives and peptide analogs.
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