Cbz-4-Bromo-D-Phenylalanine is a Cbz-protected, halogenated phenylalanine derivative in which the side chain bears a para-bromo substituent on the aromatic ring and the alpha-amino acid backbone is present as a D stereoisomer. The molecule contains a carbobenzyloxy (Cbz) protecting group on the amino functionality, leaving the carboxyl group unprotected for coupling chemistry, while the aromatic side chain provides a hydrophobic, electron-withdrawing bromo handle for further derivatization or selective reactivity. In peptide synthesis workflows, this protected amino acid is used as a building block to introduce a bromo-substituted phenylalanine residue under controlled chemoselectivity, and it can also serve in chemical biology and labeling contexts where an aryl bromide functional handle is required for subsequent conjugation or cross-coupling strategies.
CAT No: CP11209
Cbz-4-Bromo-D-Phenylalanine is a D-configured phenylalanine derivative bearing a benzyloxycarbonyl (Cbz) protecting group on the amino functionality and a para-bromine substituent on the aromatic side chain. The molecule contains a stereogenic center at the alpha carbon of the D-phenylalanine backbone, enabling stereochemically defined incorporation into peptide sequences or conversion into chiral intermediates. The Cbz group provides an N-protected handle compatible with standard peptide coupling conditions, while the aryl bromide acts as a chemically addressable electrophile for cross-coupling and subsequent functional-group diversification. The combined protected amine and aryl bromide functionality makes the compound suitable for downstream derivatization routes that preserve stereochemical integrity during amino acid intermediate preparation.
1. Peptide Synthesis
Cbz-4-Bromo-D-Phenylalanine supports peptide building-block workflows in peptide synthesis and peptidomimetic assembly, where the Cbz-protected amine functions as a stable N-terminus during coupling chemistry. The D-phenylalanine stereocenter and the para-brominated aromatic side chain allow stereodefined incorporation while introducing a latent functional handle for later diversification of side-chain electronics and binding properties. The aryl bromide can be carried through protected-amino-acid handling steps and then transformed after peptide assembly, enabling late-stage functionalization strategies. The resulting peptide analogs can be used to generate structure-defined libraries for medicinal chemistry and chemical biology studies that require controlled aromatic substitution patterns.
2. Side-Chain Functionalization
Cbz-4-Bromo-D-Phenylalanine is well suited for side-chain functionalization chemistry in synthetic organic synthesis, leveraging the aryl bromide as a reactive site for palladium-catalyzed cross-coupling reactions. The para-bromine substituent on the phenyl ring can be converted into aryl-aryl linkages, heteroaryl motifs, or other substituted aromatic frameworks while the Cbz-protected amine helps maintain chemoselectivity during intermediate transformations. The D-configuration at the alpha carbon provides a stereochemically defined chiral scaffold, which is particularly relevant when generating unnatural amino acid derivatives for peptide analogs. Downstream products from these transformations can serve as refined amino acid side-chain analogs for SAR studies, receptor-binding probes, and synthetic fragment construction.
3. Chiral Amino Acid Intermediate
Cbz-4-Bromo-D-Phenylalanine functions as a chiral amino acid intermediate for stereoselective synthesis planning, combining an N-protecting group with a defined D-amino acid backbone. The Cbz group can be removed under appropriate conditions to expose the free amine when switching from protected amino acid handling to coupling or conjugation steps in a synthetic sequence. The presence of both a stereocenter and an aryl bromide enables modular route design, where stereochemical control is maintained while the aromatic functionality is tuned through electrophile-driven derivatization. The compound can therefore be employed to prepare protected amino acid derivatives, chiral building blocks, and downstream intermediates used in fine chemical synthesis and peptide construction.
4. Chemical Biology Probes
Cbz-4-Bromo-D-Phenylalanine can be applied to chemical biology workflows that require aromatic substitution control and chemically addressable functional handles for probe generation. The protected amine and D-phenylalanine backbone support incorporation into peptide-based probes, while the para-brominated phenyl ring can be transformed into bioorthogonal or affinity-modulating substituents depending on the coupling partner chosen in later steps. The Cbz protection strategy helps maintain compatibility with peptide coupling chemistry and protects the amino group during intermediate synthesis and purification. Resulting modified amino acid or peptide probe constructs can be used to interrogate binding interactions, map recognition motifs, or generate labeled analogs for biochemical investigation.
5. Pharmaceutical Manufacturing Intermediates
Cbz-4-Bromo-D-Phenylalanine is suitable for industrial intermediate preparation in pharmaceutical manufacturing contexts where protected amino acid building blocks are produced and then converted into defined peptide or peptidomimetic fragments. The Cbz-protected amine supports controlled handling and minimizes side reactions during upstream synthesis, while the aryl bromide provides a route to standardized substituted aromatic variants used in consistent downstream material generation. D-stereochemistry is maintained through the intermediate stage, aligning with process requirements for stereochemically defined inputs into peptide construction. The compound can be incorporated into manufacturing supply chains for fine chemical synthesis of chiral amino acid derivatives and protected building blocks used in larger-scale peptide assembly programs.
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