Cbz-3-Bromo-L-Phenylalanine is a Cbz-protected, L-phenylalanine-derived amino acid bearing a bromine substituent at the 3-position of the aromatic side chain, placing it within the class of halogenated, protected amino acid building blocks for peptide chemistry. The molecule contains an N-Cbz carbamate protecting group on the amino functionality and a free carboxylic acid, while the benzyl-like aromatic ring features the 3-bromo substituent that provides a halogenated handle for subsequent chemical transformations or analytical differentiation. In synthesis, it is employed as a protected amino acid intermediate to control chemoselectivity during stepwise peptide assembly and to introduce a brominated phenylalanine residue into peptide structures for structure-activity studies, labeling strategies, or post-synthetic derivatization.
CAT No: CP11108
Cbz-3-Bromo-L-Phenylalanine is an L-phenylalanine derivative bearing a benzyloxycarbonyl (Cbz) protecting group on the amino functionality and a bromine substituent at the 3-position of the aromatic ring. The molecule retains the amino acid backbone with a free carboxylic acid suitable for amide formation while the aromatic bromide provides a distinct electrophilic handle for cross-coupling and selective functional-group elaboration. The stereogenic center at the alpha-carbon is configured as L, supporting stereochemically defined peptide coupling and downstream derivatization. Aromatic bromination combined with N-Cbz protection yields a stable chiral amino acid intermediate that can be carried through protected amino acid synthesis, peptide building block preparation, and synthetic diversification.
1. Peptide Synthesis
Cbz-3-Bromo-L-Phenylalanine supports peptide building block preparation where the Cbz-protected alpha-amino group participates in standard peptide coupling chemistry after activation of the carboxyl group. The L-configuration at the stereocenter enables stereodefined incorporation into peptide chains, while the aromatic bromide can be retained during coupling to preserve a later functionalization site. Cbz protection provides compatibility with common peptide assembly conditions and can be removed under hydrogenolysis to generate a free amine for subsequent chain extension or fragment ligation. The resulting bromo-phenylalanine-containing peptides and peptide fragments can be used to probe aromatic side-chain effects, generate halogenated analogs for SAR studies, and support iterative peptide analog construction in synthetic peptide workflows.
2. Side-Chain Functionalization
Cbz-3-Bromo-L-Phenylalanine serves as a chiral aromatic halide intermediate for side-chain functionalization strategies that convert the 3-bromophenyl motif into substituted phenyl derivatives. The Cbz-protected amine and free carboxyl group allow orthogonal handling: aromatic transformation can be performed while maintaining the amino acid functionality for later coupling, or the carboxyl group can be temporarily masked to enable selective chemistry. Halogen-to-heteroatom or halogen-to-carbon bond formation via palladium-catalyzed cross-coupling can introduce aryl, heteroaryl, or alkenyl substituents, generating unnatural amino acid analogs for chemical biology and peptidomimetic design. Downstream, the modified aromatic side chain can be used to tune hydrophobicity, electronics, and binding-site interactions in structure-activity relationship studies and molecular scaffold diversification.
3. Chiral Cross-Coupling Intermediate
Cbz-3-Bromo-L-Phenylalanine functions as a stereochemically defined chiral building block for process-relevant synthesis of functionalized aromatic amino acid derivatives. The combination of an L-amino acid core with a reactive aromatic bromide enables incorporation of the bromoaryl handle into manufacturing routes that require late-stage diversification of fine chemicals. Cbz protection stabilizes the amine during coupling and supports controlled conversion to N-unprotected amino acid derivatives when hydrogenolysis or alternative deprotection strategies are integrated into the synthetic sequence. The resulting functionalized products can serve as intermediates for pharmaceutical intermediate preparation, peptidomimetic construction, and chiral ligand or scaffold generation where retention of the alpha-stereocenter is required.
4. Chemical Biology And SAR Studies
Cbz-3-Bromo-L-Phenylalanine can be applied in chemical biology research and structure-activity relationship studies to generate halogenated amino acid analogs and peptide mimics with defined aromatic substitution patterns. The protected amine and carboxylic acid enable controlled incorporation into peptide-like structures, while the 3-bromophenyl group provides a handle for subsequent derivatization into bioorthogonal tags, binding-site probes, or electronically tuned aromatic variants. Stereochemical fidelity of the L-alpha-carbon supports meaningful comparisons across analog series where side-chain electronics and sterics are varied while the backbone configuration remains constant. Downstream derivatives prepared from this intermediate can be used to map aromatic contributions to molecular recognition, support SAR panel synthesis, and generate reagent sets for biochemical target interrogation.
5. Pharmaceutical Intermediate Preparation
Cbz-3-Bromo-L-Phenylalanine is suitable for pharmaceutical intermediate preparation where protected amino acid chemistry and aromatic functional-group transformation are combined in a single chiral platform. The Cbz group provides an N-protecting strategy that can be carried through synthetic steps and removed when conversion to free amines is required for further coupling, salt formation, or incorporation into larger scaffolds. The free carboxylic acid can be converted into activated derivatives for amide bond formation, supporting integration into medicinal chemistry fragments and peptide-like structures. The aromatic bromide enables manufacturing-compatible diversification toward substituted phenyl motifs commonly used in fine chemical synthesis, enabling scalable access to bromoaryl-containing intermediates for downstream synthetic organic chemistry and applied product development.
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