Cbz-3,4-Dichloro-L-Phenylalanine is a Cbz-protected, halogenated phenylalanine derivative featuring a benzyl oxycarbonyl (Cbz) protecting group on the amino functionality and a side chain bearing two chlorine substituents at the 3- and 4-positions of the aromatic ring. The molecule contains both an amino acid framework with a free carboxylic acid and a stereocenter specified as L, while the dichloro-substituted phenyl side chain provides increased hydrophobicity and altered aromatic electronics relative to unsubstituted phenylalanine. In peptide chemistry and chemical biology, it is used as a protected amino acid building block for incorporating a sterically and electronically modified phenylalanine residue into peptides or peptide-related intermediates, and it can also serve as a defined substrate for structure-activity and labeling studies where halogenated aromatic side chains are required.
CAT No: CP12408
Cbz-3,4-Dichloro-L-Phenylalanine is an L-phenylalanine derivative bearing a benzyloxycarbonyl (Cbz) protecting group on the amino functionality and a 3,4-dichloro-substituted phenyl side chain that increases halogenated aromatic character and influences steric and electronic properties. The molecule contains a stereogenic center at the alpha carbon consistent with L-configuration, together with a carboxylic acid functionality suitable for standard peptide coupling chemistry after activation. The Cbz group provides an acid-stable, base-tolerant N-protection handle that can be removed under hydrogenolysis conditions, enabling controlled peptide assembly and later deprotection. The dichloroaryl side chain can participate in halogen-directed reactivity and downstream derivatization, making the compound a practical chiral amino acid intermediate for building halogenated aromatic motifs in peptide and small-molecule frameworks.
1. Peptide Synthesis
Cbz-3,4-Dichloro-L-Phenylalanine is used in peptide building workflows where an N-Cbz protected L-amino acid is required for stepwise amide bond formation. The Cbz-protected amine and carboxylic acid enable peptide coupling strategies that preserve the L-stereocenter while installing the protected residue at a defined position in a growing chain. The 3,4-dichloro-substituted phenyl side chain functions as a robust hydrophobic and electron-withdrawing aromatic element that can tune local conformation and binding interactions in peptide analogs. Controlled Cbz deprotection supports sequential coupling cycles, allowing synthesis of halogenated peptide segments and peptide conjugation precursors from a single chiral building block. The compound therefore serves as a structurally specific intermediate for constructing peptide libraries and sequence-defined peptidic scaffolds.
2. Side-Chain Functionalization
Cbz-3,4-Dichloro-L-Phenylalanine is applied in synthetic organic chemistry for preparing halogenated aromatic intermediates that can undergo further functional group transformations at the dichloro positions. The two chlorine atoms on the phenyl side chain provide handles for substitution, cross-coupling, and selective derivatization routes that introduce aryl, heteroaryl, or other substituents while maintaining the amino acid backbone for downstream incorporation. The preserved alpha-amino acid stereochemistry and N-Cbz protection allow chemists to carry out side-chain modifications without exposing the amine prematurely. The resulting substituted phenylalanine derivatives can be used to generate structure-defined analogs for SAR studies, receptor-binding probes, or peptidomimetic fragments. This makes the compound a useful platform for amino acid derivatization strategies that link stereochemical control with aromatic functionalization.
3. Peptidomimetics And SAR
Cbz-3,4-Dichloro-L-Phenylalanine is used in medicinal chemistry research programs focused on peptidomimetic construction and structure-activity relationship studies. The L-phenylalanine core provides a stereochemically defined alpha-amino acid motif, while the Cbz group supports incorporation into peptide-like structures that later undergo deprotection or conversion into amide-linked scaffolds. The 3,4-dichloroaryl side chain can modulate hydrophobicity, polarizability, and aromatic electronics, which are common parameters examined when mapping how side-chain substitution influences binding and conformational preferences. The compound can be employed to assemble analog series where halogen patterns are systematically varied by subsequent coupling or side-chain modification steps. Downstream derivatives generated from this chiral intermediate can serve as defined fragments for SAR mapping and molecular design workflows.
4. Chemical Biology Probes
Cbz-3,4-Dichloro-L-Phenylalanine is suitable for chemical biology applications that require incorporation of a protected, stereodefined amino acid into probe molecules. The N-Cbz protection allows controlled assembly of labeled peptides or peptide mimics, while the carboxylic acid functionality supports conversion into activated intermediates for conjugation chemistry. The dichloroaryl side chain can provide a chemically stable aromatic element that can be retained through probe synthesis, enabling subsequent attachment of affinity tags or reporter groups at other positions of a probe scaffold. The ability to remove Cbz under hydrogenolysis conditions supports late-stage unveiling of the amine for further conjugation or for generating reactive intermediates during probe construction. This aligns the compound with workflows that build structurally defined biomolecular probes and peptide-based recognition elements.
5. Pharmaceutical Intermediate Preparation
Cbz-3,4-Dichloro-L-Phenylalanine is used as a chiral amino acid intermediate in pharmaceutical intermediate preparation where protected amino acid chemistry and halogenated aromatic motifs are required. The Cbz-protected amine and carboxylic acid enable integration into multi-step manufacturing routes that assemble amide linkages while maintaining stereochemical integrity at the alpha carbon. The 3,4-dichlorophenyl side chain is compatible with industrial fine chemical strategies that rely on robust aromatic handles for later diversification into substituted aryl or heteroaryl groups. Controlled deprotection of the Cbz group supports downstream coupling to other building blocks, including conversion into drug-like fragments or advanced intermediates for medicinal chemistry programs. The compound thus functions as a process-compatible chiral intermediate for generating halogenated amino acid derivatives used in applied synthesis planning.
6. Industrial Peptide Building Blocks
Cbz-3,4-Dichloro-L-Phenylalanine is employed in industrial peptide building block manufacturing where N-protected amino acids with defined stereochemistry are required for reproducible coupling chemistry. The Cbz group provides a widely used protection strategy that can withstand common conditions during peptide assembly and can be removed cleanly when the process calls for amine liberation. The dichloro-substituted phenyl side chain contributes a stable aromatic functionality that can survive peptide synthesis steps and can influence solubility and material properties of peptide products or peptide-derived intermediates. The compound's structure supports its use in automated or semi-automated peptide synthesis workflows that require consistent reactivity of protected amino acid inputs. This positions the material as a practical chiral input for producing halogenated peptide segments and related amino acid-derived intermediates at scale.
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