Cbz-3,4-Dichloro-D-Phenylalanine is a protected, non-proteinogenic amino acid derivative featuring a benzyl-protected carboxamide equivalent (Cbz) on the amino acid nitrogen and a phenylalanine backbone bearing two chlorine substituents at the 3 and 4 positions of the aromatic side chain. The molecule contains an amino acid framework with a Cbz-protected amine and a free carboxyl group, with the side chain retaining a chlorinated phenyl functionality that can modulate hydrophobicity and aromatic interactions, while the D stereochemical designation indicates the configuration at the alpha carbon. In peptide-chemistry workflows, this protected analogue functions as a stepwise coupling building block for incorporating a halogenated, aromatic side chain into peptides or peptide-related intermediates, and it can also be used in structure-activity studies or analytical method development where controlled introduction of chlorinated phenylalanine motifs is required.
CAT No: CP12409
Cbz-3,4-Dichloro-D-Phenylalanine is a Cbz-protected D-phenylalanine derivative bearing two chlorine substituents on the aromatic ring at the 3- and 4-positions. The molecule contains a stereogenic center at the amino acid alpha-carbon with D-configuration, a benzyloxycarbonyl (Cbz) carbamate that masks the amino functionality for controlled peptide coupling, and a free carboxyl group suitable for conversion into activated esters or amide-forming derivatives. The dichloro-substituted phenyl side chain increases hydrophobicity and provides handles for electrophilic aromatic substitution, halogen-directed derivatization, and downstream cross-coupling chemistry. The combination of a protected amine, an acid handle, and a defined aromatic substitution pattern makes the compound a practical chiral amino acid intermediate for peptide building block preparation and medicinal chemistry scaffold elaboration.
1. Peptide Synthesis
Cbz-3,4-Dichloro-D-Phenylalanine is applied in peptide synthesis workflows where C-terminal or side-chain functionalized sequences require a D-amino acid building block. The Cbz carbamate protects the amino group during coupling, while the carboxylic acid enables peptide bond formation through standard activated-carboxyl strategies compatible with protecting-group orthogonality. The 3,4-dichloro-phenyl side chain can be incorporated to tune steric and hydrophobic character in peptide analogs and peptidomimetics, including sequences designed for altered protease recognition. The defined D-stereochemistry supports stereocontrolled assembly of chiral peptide frameworks and provides a stable intermediate for subsequent deprotection and chain extension.
2. Peptidomimetics And SAR
Cbz-3,4-Dichloro-D-Phenylalanine is utilized in peptidomimetic construction and structure-activity relationship studies where aromatic halogenation is used to modulate binding-site interactions. The dichloro-substituted phenyl group provides a distinctive electronic and steric profile, while the D-configuration at the alpha-carbon can be leveraged to influence conformational preferences and proteolytic stability in analog series. The Cbz-protected amine supports stepwise synthesis of constrained or substituted peptide-like scaffolds, enabling systematic variation of side-chain electronics without disturbing the stereocenter. The resulting chiral intermediate can be carried into downstream functionalization, including conversion into additional side-chain derivatives for SAR mapping.
3. Side-Chain Functionalization
Cbz-3,4-Dichloro-D-Phenylalanine is suitable for side-chain functionalization strategies that exploit aryl chloride reactivity for later diversification. The 3,4-dichloro aromatic ring can participate in halogen-directed transformations such as cross-coupling to install aryl, heteroaryl, or alkyl substituents, while retaining the amino acid backbone for conversion into new amide or peptide contexts. The Cbz carbamate and carboxylic acid functionality enable staged protection management, allowing selective modification of the aromatic ring prior to or after peptide coupling steps. The stereodefined D-amino acid framework supports generation of libraries of halogenated analogs that can be used as biochemical research intermediates and synthetic organic chemistry building blocks.
4. Chemical Biology Probes
Cbz-3,4-Dichloro-D-Phenylalanine is applied in chemical biology research for preparing chiral amino acid derivatives that can be incorporated into labeled peptides or affinity reagents. The protected amine (Cbz) supports controlled incorporation into peptide constructs, while the aromatic dichloro pattern can be retained as a hydrophobic anchor or a site for subsequent derivatization to introduce reporter-compatible substituents. The D-configuration can be used to generate peptide analogs with altered stability toward enzymatic degradation, which is relevant for probe persistence in biochemical assays. The compound's acid functionality also supports conversion into activated intermediates for conjugation to linkers, enabling downstream biomolecule modification strategies.
5. Pharmaceutical Intermediate Preparation
Cbz-3,4-Dichloro-D-Phenylalanine is relevant to pharmaceutical intermediate preparation and fine chemical synthesis where chiral, protected amino acids serve as controlled inputs for medicinal chemistry. The Cbz-protected amine provides a predictable protection strategy during multi-step synthesis, while the carboxylic acid can be transformed into coupling-ready derivatives for incorporation into larger molecules. The dichloro-substituted phenyl side chain offers a chemically meaningful motif for scaffold diversification through selective aromatic substitution or coupling chemistry. The stereodefined D-amino acid intermediate can be routed into peptide-like candidates, peptidomimetic fragments, or other chiral amide-containing structures, aligning with process chemistry needs for reproducible intermediate handling and downstream derivatization.
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