Cbz-2,3-Dichloro-D-Phenylalanine is a Cbz-protected, non-natural amino acid derivative featuring a D-phenylalanine backbone with two chloro substituents at the 2- and 3-positions of the aromatic ring. The molecule contains a Cbz carbamate protecting group on the amino functionality, a free carboxyl group, and a chlorinated phenyl side chain that bears electron-withdrawing substituents while retaining the stereochemical configuration indicated by the D designation. In peptide chemistry and chemical biology, this protected amino acid is used as a building block for incorporating a halogenated phenylalanine analogue into peptide sequences and for structure-activity or labeling studies where aryl halogens provide defined physicochemical and analytical handles.
CAT No: CP12009
Cbz-2,3-Dichloro-D-Phenylalanine is an N-Cbz protected D-phenylalanine derivative bearing vicinal 2,3-dichloro substitution on the α-carbon framework, creating a chiral amino acid intermediate with enhanced electrophilic character at the halogenated positions. The molecule contains a carbamate-protected amine (Cbz), a free carboxylic acid functionality suitable for activation and coupling, and a benzyl carbamate aromatic moiety that can be removed under hydrogenolysis conditions to regenerate the corresponding D-amine. The two chlorine atoms at C2 and C3 are stereochemically defined relative to the D-configuration, enabling controlled downstream transformations such as selective dehalogenation, nucleophilic substitution, and incorporation into halogenated peptide or peptidomimetic scaffolds. The combination of a protected amino group and a halogenated α-framework makes the compound a practical chiral building block for amino acid derivatization and peptide chemistry where stereochemical fidelity and functional-group compatibility are required.
1. Peptide Synthesis
Cbz-2,3-Dichloro-D-Phenylalanine supports peptide building block preparation for solid-phase or solution-phase peptide coupling by providing a carbamate-protected nitrogen and a carboxylic acid handle for amide bond formation. The D-configuration and vicinal dichloro substitution can be retained through standard peptide coupling conditions when orthogonal protection strategies are used for other residues, allowing stereodefined incorporation of a halogenated amino acid into peptide chains. The Cbz group participates in standard protection/deprotection workflows, enabling orthogonal N-deprotection after assembly to support iterative elongation or fragment coupling. Downstream, the incorporated dichloro motif can serve as a chemically addressable element for post-assembly diversification, including dehalogenation or substitution steps that generate peptide analogs with altered physicochemical properties.
2. Peptidomimetics And SAR Studies
Cbz-2,3-Dichloro-D-Phenylalanine functions as a chiral scaffold element for peptidomimetic construction and structure-activity relationship studies where halogenated α-amino acid residues modulate sterics and electronic features. The protected amine and carboxyl group allow conversion into coupling-ready formats that integrate the dichloro-D-phenylalanine motif into constrained analogs, including side-chain modified backbones and halogen-rich pharmacophore mimics. The vicinal dichloro pattern can be leveraged as a tunable handle for subsequent chemical transformations, supporting SAR workflows that compare halogenated versus partially transformed variants. The resulting halogenated peptide analogs can be used to map how stereodefined halogen placement influences binding-site complementarity and molecular recognition in biochemical assay panels.
3. Side-Chain Functionalization
Cbz-2,3-Dichloro-D-Phenylalanine can be employed for amino acid derivatization routes that exploit the reactivity of the C2/C3 chlorine atoms to introduce new substituents while preserving the stereogenic D-center. The N-Cbz protection strategy enables selective functional group manipulation at the halogenated positions without requiring premature exposure of the amino group, supporting controlled nucleophilic substitution or dehalogenation sequences in downstream synthetic steps. The carboxylic acid functionality can be activated for conversion into esters or amides, providing additional handles for orthogonal protection and later coupling into larger molecules. The ability to generate stereodefined, halogen-to-substituent transformed derivatives makes this compound suitable for producing functionalized amino acid intermediates used in fine chemical synthesis and specialized scaffold assembly.
4. Chemical Biology Labeling
Cbz-2,3-Dichloro-D-Phenylalanine supports chemical biology workflows that require incorporation of a defined halogenated amino acid into peptide-like probes for tracking and mechanistic studies. The protected amine and carboxyl group allow integration into peptide conjugates or probe scaffolds through amide coupling, while the dichloro α-framework can serve as a chemically addressable element for subsequent derivatization to introduce reporter-compatible functionalities. The stereochemical integrity of the D-amino acid can be important for maintaining binding specificity in target recognition studies that are sensitive to stereochemistry. Downstream, the resulting labeled or derivatized biomolecule analogs can be used as research intermediates for studying substrate recognition, protease selectivity, and structure-dependent chemical reactivity.
5. Process Chemistry Intermediate
Cbz-2,3-Dichloro-D-Phenylalanine is suitable as a chiral amino acid intermediate for process chemistry intermediate preparation where robust protection-group handling and defined stereochemistry are required. The Cbz carbamate provides a stable N-protection state during activation of the carboxylic acid and coupling operations, while hydrogenolysis-compatible deprotection supports controlled conversion to the free amino form when needed for downstream manufacturing steps. The dichloro α-substitution can enable downstream conversion into a family of structurally related intermediates, supporting route design that reuses a common chiral feedstock to access multiple halogenated or transformed derivatives. The compound's amino acid framework and functional-group pattern make it compatible with industrial-scale fine chemical synthesis strategies focused on stereodefined intermediate supply for peptide building block manufacturing and derivative generation.
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