Cbz-2,5-Dichloro-L-Phenylalanine is a protected, halogenated phenylalanine derivative in which the α-amino group is carbobenzyloxy (Cbz/Cbz) protected and the aromatic side chain bears two chlorine substituents at the 2- and 5-positions. The molecule contains both an α-carboxylic acid functional group and a Cbz-protected amino functionality, with the side chain retaining the L-phenylalanine backbone stereochemical designation as indicated by the product name. In peptide chemistry and chemical biology workflows, this protected amino acid is used as a building block for incorporating a 2,5-dichloro-substituted phenylalanine residue into peptides or peptide-related intermediates, and the halogenated aromatic ring provides a distinct handle for structure-activity studies, conjugation strategies, or analytical method development.
CAT No: CP12208
Cbz-2,5-Dichloro-L-Phenylalanine is an L-phenylalanine derivative bearing a benzyloxycarbonyl (Cbz) N-protecting group and two chlorine substituents on the aromatic ring at the 2- and 5-positions relative to the side-chain, creating a defined, electron-withdrawing, halogenated aryl environment. The molecule retains the amino acid core with a stereogenic center at the alpha carbon, providing a chiral building block compatible with stereocontrolled peptide assembly. The Cbz-protected amine and the carboxylic acid functionality (or acid-form equivalent depending on formulation) support standard peptide coupling workflows while the dichloro substitution modulates aromatic reactivity, hydrophobicity, and potential for further functional group transformations. The halogenated phenyl motif can function as a stable aryl handle for downstream derivatization, including cross-coupling or selective aromatic modifications, making the compound suitable as a protected amino acid intermediate in synthetic and biochemical research.
1. Peptide Synthesis
Cbz-2,5-Dichloro-L-Phenylalanine is used in peptide synthesis to introduce a halogenated phenylalanine residue with defined L-stereochemistry into protected peptide chains. The Cbz-protected N-terminus supports peptide coupling chemistry while the carboxyl group participates as the acylating partner, enabling stepwise construction of oligopeptides and peptide fragments. The 2,5-dichloro aromatic side chain can influence coupling outcomes and subsequent peptide solubility, and it can be retained through multiple synthetic steps to generate halogenated peptide analogs. Downstream deprotection of the Cbz group allows sequential N-terminal functionalization, supporting iterative peptide assembly and purification-ready protected intermediates in synthetic peptide workflows.
2. Peptidomimetics And SAR
Cbz-2,5-Dichloro-L-Phenylalanine is applied in peptidomimetic design and structure-activity relationship studies where halogenated aromatic side chains are used to tune binding interactions and physicochemical properties. The rigid, dichloro-substituted phenyl ring provides a stereochemically consistent hydrophobic and electron-withdrawing motif that can be carried into peptide analogs or constrained scaffolds. The protected amino acid format enables incorporation into peptide-like structures through standard coupling and subsequent functional group manipulations, including side-chain retention for later diversification. The resulting halogenated derivatives can serve as comparative SAR building blocks for mapping how aromatic substitution patterns affect molecular recognition in lead optimization programs.
3. Side-Chain Functionalization
Cbz-2,5-Dichloro-L-Phenylalanine supports side-chain functionalization strategies in synthetic organic chemistry by providing a protected amino acid bearing two aryl chlorides as transformation handles. The Cbz group allows orthogonal protection management, letting chemists perform aromatic modifications under conditions that preserve the amino acid stereocenter and peptide-ready functionality. The 2,5-dichloro substitution pattern can be exploited for selective or sequential aromatic derivatization, generating aryl-substituted analogs such as substituted aryl ethers, aryl amines, or cross-coupled heteroaryl variants while maintaining the amino acid core for downstream coupling. The resulting functionalized amino acid derivatives can be used to prepare diversified libraries and intermediate precursors for fine chemical synthesis and applied scaffold generation.
4. Chemical Biology Probes
Cbz-2,5-Dichloro-L-Phenylalanine is suitable for chemical biology research that requires incorporation of a halogenated amino acid into peptide-based probes or affinity reagents. The L-configuration and protected amine enable controlled incorporation into probe scaffolds where the dichloro aromatic ring contributes to hydrophobic contacts and can serve as a stable, non-labile reporter element during biochemical assays. The Cbz-protected amino acid can be assembled into labeled or tag-bearing peptides through peptide coupling chemistry, followed by deprotection and conjugation steps to attach detection handles or biomolecule-binding motifs. The halogenated aromatic residue can also assist in designing probes for target engagement studies by providing a defined structural element that remains intact through typical derivatization and purification workflows.
5. Pharmaceutical Intermediate Preparation
Cbz-2,5-Dichloro-L-Phenylalanine is employed as a protected amino acid intermediate in pharmaceutical manufacturing and process chemistry for producing halogenated peptide fragments and related building blocks. The Cbz-protected amine and amino acid backbone support scalable peptide coupling and controlled deprotection sequences, aligning with industrially relevant synthetic planning for protected intermediates. The dichloro aromatic side chain can be retained to deliver defined substitution patterns in drug-like peptides, peptide conjugates, or peptidomimetic precursors, reducing the need for late-stage aromatic remodeling. The compound's chiral, protected structure makes it compatible with downstream conversion into standardized intermediates for further functionalization and formulation-oriented material generation within applied chemical manufacturing routes.
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