Cbz-4-Chloro-D-Phenylalanine is a protected, non-natural amino acid derivative in which the phenylalanine backbone bears a para-chloro substituent on the aromatic side chain and is present in the D stereochemical form as indicated by the product name. The amino group is protected as a benzyloxycarbonyl (Cbz) carbamate, while the molecule also contains a free carboxylic acid functional group, and the chlorinated aromatic side chain provides distinct electron-withdrawing character and altered hydrophobicity relative to unsubstituted phenylalanine. As a Cbz-protected amino acid, it is used as a building block for stepwise peptide synthesis and for preparing chlorinated phenylalanine-containing peptide analogues for structure-activity studies and analytical method development.
CAT No: CP11609
Cbz-4-Chloro-D-Phenylalanine is a D-configuration phenylalanine derivative bearing a benzyloxycarbonyl (Cbz) protecting group on the amino function and a para-chloro substituent on the aromatic side chain. The molecule combines a chiral alpha-carbon with an aniline-like aromatic ring that can participate in electrophilic aromatic substitution, halogen-directed reactivity, and π-stacking interactions relevant to peptide and peptidomimetic scaffold design. The Cbz carbamate is stable under many peptide-coupling conditions yet can be removed under hydrogenolysis or strong hydrogen-activating conditions, enabling orthogonal protection strategies during protected amino acid synthesis. The aryl chloride provides a handle for downstream cross-coupling or selective functional group transformation while maintaining the stereochemical integrity of the D-amino acid building block.
1. Peptide Synthesis
Cbz-4-Chloro-D-Phenylalanine supports peptide building block workflows in solid-phase or solution-phase peptide synthesis where a protected D-amino acid is required. The Cbz-protected amine facilitates standard peptide coupling chemistry while the carboxyl group remains available for activation and amide bond formation, enabling controlled incorporation at defined positions within peptide sequences. The D-stereochemistry can be used to tune backbone conformation, protease resistance, and side-chain presentation in peptide analog libraries. The para-chloro aromatic substituent can further influence coupling outcomes, steric environment, and subsequent derivatization steps after deprotection and purification.
2. Peptidomimetics And SAR
Cbz-4-Chloro-D-Phenylalanine is applicable to peptidomimetic construction and structure-activity relationship studies where aromatic halogenation is used to modulate binding interactions. The protected amino acid framework allows sequential assembly into peptide-like scaffolds, while the para-chloro substituent can serve as a pharmacophore element for halogen bonding and hydrophobic contact tuning. The D-configuration enables stereochemical variation without changing the side-chain identity, supporting SAR campaigns that compare L- and D-incorporation effects on conformational preferences. Downstream aryl chloride functionalization via cross-coupling can generate diversified analogs for iterative SAR mapping and medicinal chemistry intermediate preparation.
3. Side-Chain Functionalization
Cbz-4-Chloro-D-Phenylalanine functions as a chiral aromatic intermediate for side-chain functionalization strategies that leverage the para-chloro substituent. The aryl chloride can undergo transition-metal-catalyzed cross-coupling to introduce substituents such as alkyl, aryl, or heteroaryl groups, enabling controlled elaboration of the phenylalanine side chain after peptide assembly or independent derivatization. The Cbz carbamate provides a protected nitrogen handle that can be retained during certain transformations and then removed to reveal the free amine for subsequent conjugation or further coupling. The resulting functionalized D-phenylalanine derivatives can be used to generate chemical probes, linker-bearing building blocks, and non-natural amino acid analogs for downstream synthetic programs.
4. Chemical Biology Labeling
Cbz-4-Chloro-D-Phenylalanine can be employed in chemical biology workflows that require incorporation of a stereodefined aromatic amino acid into tagged peptides or probe molecules. The Cbz-protected amine and carboxyl functionality enable stepwise peptide coupling to position the D-chiral center at a defined locus, supporting controlled presentation of the aromatic chloride motif within a biorecognition context. The para-chloro group may serve as a synthetic handle for building linker-bearing derivatives that later enable conjugation to affinity tags, fluorophores, or affinity-reactive moieties. The compound's protected-amino acid nature supports compatibility with orthogonal deprotection schedules used to generate labeled biomolecule constructs for mechanistic studies.
5. Pharmaceutical Intermediate Preparation
Cbz-4-Chloro-D-Phenylalanine is suitable for pharmaceutical intermediate preparation within fine chemical synthesis programs that require chiral, protected amino acid building blocks. The Cbz carbamate protects the amino group to maintain chemoselectivity during carboxyl activation and coupling steps, while the D-configuration supports stereochemically defined intermediate generation for downstream medicinal chemistry routes. The aryl chloride substituent enables diversification through cross-coupling chemistry, allowing access to substituted aromatic analogs that can be carried into higher-complexity intermediates. The compound's dual role as a protected amino acid and a functionalized aromatic intermediate aligns with process chemistry needs for scalable, modular synthesis of non-natural amino acid derivatives.
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