Cbz-2,4-Dichloro-L-Phenylalanine is a protected, non-natural amino acid derivative belonging to the phenylalanine family, featuring a phenyl ring substituted with chlorine atoms at the 2 and 4 positions and an L-stereochemical designation as indicated by the name. The molecule bears a benzyl-type carbamate protecting group (Cbz) on the amino functionality while retaining the carboxylic acid group, and its chlorinated aromatic side chain provides increased hydrophobicity and halogen-bonding character relative to unsubstituted phenylalanine. As a stepwise peptide-synthesis intermediate, the Cbz-protected amino acid supports chemoselective coupling strategies for incorporating a sterically and electronically modified phenylalanine residue into peptides and for preparing halogenated analogues used in structure-activity studies or chemical labeling workflows.
CAT No: CP12108
Cbz-2,4-Dichloro-L-Phenylalanine is an N-Cbz protected L-phenylalanine derivative bearing two chlorine substituents at the 2- and 4-positions of the aromatic ring. The molecule combines a stereodefined α-amino acid framework with an electron-poor, halogenated side chain that can influence aromatic reactivity, conformational preferences, and downstream derivatization patterns. The benzyloxycarbonyl (Cbz) group provides stable N-protection compatible with peptide coupling conditions and can be removed by hydrogenolysis to regenerate the free amino functionality. The dichloro-substituted phenyl side chain functions as a chemically persistent motif that can be carried through peptide synthesis, used for selective transformations, and serves as a chiral intermediate for further amino acid modification strategies.
1. Peptide Synthesis
Cbz-2,4-Dichloro-L-Phenylalanine is used in peptide building workflows where N-Cbz protection supports standard amide bond formation while maintaining the L-configuration at the α-carbon. The protected amino acid framework enables incorporation at defined positions within peptide sequences, and the halogenated phenyl side chain can modulate hydrophobicity and aromatic interactions in the resulting peptide. Cbz protection allows orthogonal handling relative to other protecting groups, supporting stepwise assembly and subsequent deprotection to reveal the coupling-ready amino terminus. The resulting halogenated peptide analogs can be applied in peptide science, structure-activity relationship studies, and synthetic methodology development for amino acid substitution patterns.
2. Peptidomimetics And SAR
Cbz-2,4-Dichloro-L-Phenylalanine is applied in medicinal chemistry oriented scaffold construction where the dichloro-phenyl motif serves as a tunable aromatic element for SAR studies and peptidomimetic design. The stereodefined amino acid core provides a consistent chiral center, while the 2,4-dichloro substitution pattern can be leveraged to adjust electronic character and steric profile of the side chain in conformationally constrained analogs. Cbz protection supports controlled functional group presentation during fragment coupling, cyclization strategies, or late-stage assembly of bioactive-like constructs. Downstream derivatives prepared from this intermediate can be used to generate libraries of aromatic-substituted peptide mimics for binding and selectivity investigations.
3. Chemical Biology Labeling
Cbz-2,4-Dichloro-L-Phenylalanine is suitable for chemical biology research that requires incorporation of an aromatic, halogenated residue into peptide probes or protein-interacting ligands. The protected amino acid form supports sequential synthesis of conjugatable peptides, and the dichloro-phenyl side chain can serve as a stable handle for subsequent functional group transformations or as a recognition element within molecular probes. Cbz deprotection can be used to access the free amine for conjugation steps that produce amide-linked or other nitrogen-containing attachments to biomolecular targets. Halogenated aromatic residues introduced via this intermediate can be carried into downstream biomolecule modification workflows used for mechanistic studies and probe development.
4. Process Chemistry Intermediate
Cbz-2,4-Dichloro-L-Phenylalanine is employed as a chiral amino acid intermediate in fine chemical synthesis and process chemistry where N-protection and stereochemical integrity are required during scale-up compatible transformations. The Cbz group provides a robust protecting strategy that can withstand peptide coupling conditions and can be removed under controlled hydrogenolysis to yield the corresponding free amino acid derivative. The dichloro-substituted aromatic side chain remains chemically defined through intermediate handling, supporting reproducible downstream conversion into protected or derivatized amino acid building blocks. This structure-function combination enables manufacturing routes for halogenated amino acid derivatives used in peptide manufacturing feeds, specialty chemical production, and intermediate supply for further synthetic elaboration.
5. Side-Chain Functionalization
Cbz-2,4-Dichloro-L-Phenylalanine is used in synthetic organic chemistry for side-chain functionalization strategies that exploit the persistent dichloro-substituted aromatic ring. The amino acid stereocenter and N-Cbz protection allow the molecule to be carried through selective transformations while maintaining compatibility with coupling chemistry and protecting-group management. The aryl dichlorides can potentially undergo substitution or cross-coupling-based elaboration to install additional substituents, enabling access to functionalized phenylalanine analogs for peptide analog construction and materials-relevant aromatic motifs. Downstream products derived from these modifications can feed into combinatorial synthesis, targeted scaffold diversification, and the preparation of halogenated amino acid derivatives for applied research and industrial intermediate development.
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