Cbz-2,5-Dichloro-D-Phenylalanine is a protected D-phenylalanine derivative in which the amino group is carbobenzyloxy-protected (Cbz) and the aromatic side chain bears two chlorine substituents at the 2 and 5 positions. The molecule contains a Cbz-protected α-amino functionality and a free carboxylic acid, with the side chain retaining the phenyl ring substituted by 2,5-dichloro substituents that modulate hydrophobicity and electronic character. As a protected amino acid building block, it is used in peptide synthesis and related structure-activity or chemical biology studies where incorporation of halogenated, non-proteinogenic aromatic residues and controlled deprotection of the Cbz group are relevant for stepwise assembly of peptide-like structures.
CAT No: CP12209
Cbz-2,5-Dichloro-D-Phenylalanine is a Cbz-protected D-phenylalanine derivative bearing two chlorine substituents on the aromatic ring, creating a chiral amino acid building block with a benzyloxycarbonyl (Cbz) carbamate at the α-amino position and a free carboxylic acid suitable for peptide coupling chemistry. The D-stereocenter at the α-carbon provides defined stereochemical control for incorporation into peptide sequences and stereochemically constrained analogs. The dichloro-substituted phenyl side chain introduces increased hydrophobicity and electron-withdrawing character, which can influence amide bond formation, conformational preferences, and downstream functional transformations. The Cbz protecting group enables orthogonal deprotection strategies during protected amino acid synthesis, while the aryl chlorides can participate in cross-coupling or nucleophilic aromatic substitution routes for diversified scaffold construction.
1. Peptide Synthesis
Cbz-2,5-Dichloro-D-Phenylalanine supports peptide building block preparation for solid-phase or solution-phase assembly where a protected amino acid with a defined D-configuration is required. The Cbz carbamate masks the α-amino group for controlled amide bond formation using standard coupling chemistries, while the carboxylic acid functionality enables incorporation at a specific peptide position. The 2,5-dichloro phenyl side chain can be retained through peptide assembly to generate halogenated peptide analogs for structure-activity relationship studies and conformational probing. The resulting protected amino acid incorporation enables downstream deprotection and peptide fragment elaboration using established peptide chemistry workflows.
2. Peptidomimetics And SAR Studies
Cbz-2,5-Dichloro-D-Phenylalanine is applicable to peptidomimetic construction and medicinal chemistry research where halogenated aromatic residues are used to tune lipophilicity, binding-site interactions, and metabolic stability proxies. The D-configuration and Cbz-protected α-amino group allow stereochemically defined incorporation into peptide-like scaffolds, while the dichloro-substituted phenyl ring provides handles for additional derivatization without altering the core stereochemistry. The aryl chlorides can be leveraged to generate analog series via selective substitution or cross-coupling, supporting structure-activity relationship studies that compare side-chain electronics and steric effects. The compound thus functions as a chiral, derivatizable amino acid intermediate for constructing libraries of halogenated peptidomimetics.
3. Chemical Biology Probes
Cbz-2,5-Dichloro-D-Phenylalanine can be used in chemical biology research to prepare labeled or functionalized amino acid derivatives that map peptide recognition and protein interaction interfaces. The protected amino acid format enables stepwise synthesis of peptide conjugates where the Cbz group can be removed under standard carbamate deprotection conditions to expose the free amine for further conjugation or coupling. The dichloro aromatic side chain can serve as a stable hydrophobic motif in probes designed for controlled residence time in binding assays, while the chlorides can enable post-assembly functionalization to introduce affinity tags, reporter groups, or reactive handles. The stereodefined D-phenylalanine residue supports incorporation into protease-resistant or stereochemically constrained probe designs.
4. Side-Chain Functionalization
Cbz-2,5-Dichloro-D-Phenylalanine is suitable for side-chain functionalization strategies that convert aryl chloride substituents into diversified chemical functionalities while maintaining the amino acid backbone. The Cbz-protected α-amino group and carboxylic acid allow the molecule to be carried through synthetic sequences as a protected chiral intermediate, enabling selective transformations on the aromatic ring. The 2,5-dichloro substitution pattern can be exploited for sequential coupling or substitution to install substituents such as heteroaryl groups, alkyl/aryl fragments, or nucleophilic aromatic substitution products, generating a family of modified amino acid derivatives. Downstream, these derivatives can be reintroduced into peptide coupling steps to produce functionalized analogs for synthetic organic chemistry and biochemical research intermediate preparation.
5. Pharmaceutical Intermediate Preparation
Cbz-2,5-Dichloro-D-Phenylalanine can serve as a process-relevant chiral intermediate for manufacturing routes that require protected D-amino acid building blocks with defined stereochemistry and derivatizable aromatic functionality. The Cbz protecting group supports controlled handling of the α-amino functionality during multi-step synthesis, while the carboxylic acid provides a consistent coupling-ready handle for conversion into activated intermediates. The dichloro phenyl side chain can be retained during early stages and later transformed to meet specific structure requirements for peptide-like intermediates or halogenated scaffold components. The compound's protected amino acid structure aligns with fine chemical synthesis workflows that emphasize stereochemical fidelity and functional group compatibility across sequential operations.
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