3-Bromo-D-Phenylalanine is a non-natural, halogenated phenylalanine derivative featuring a benzyl side chain bearing a bromine substituent at the 3-position and a stereogenic center consistent with the D configuration indicated in the name. The molecule contains both an amino group and a carboxyl group on the alpha carbon, providing the typical amino acid functionality for coupling chemistry while the aryl bromide serves as a carbon-bromine handle that can participate in further derivatization or cross-coupling strategies under appropriate conditions. In biochemical and synthetic research, this amino acid is used as a building block for preparing modified peptides, for structure-activity studies that probe the effect of aryl halogen substitution, and for analytical or labeling workflows where the brominated aromatic motif provides a chemically distinguishable tag.
CAT No: CP11102
3-Bromo-D-Phenylalanine is a D-configured phenylalanine analog bearing a benzylic bromine substituent on the aromatic ring, making it a halogenated, non-proteinogenic amino acid building block for medicinal chemistry and chemical biology workflows. Its stereochemistry and aryl bromide handle support downstream derivatization via carbon-halogen functionalization, enabling the preparation of halogenated peptide analogs, constrained side-chain variants, and structure-activity relationship (SAR) libraries. Researchers select this reagent when a brominated aromatic motif and D-configuration are required to probe stereochemical effects, improve synthetic tractability, or introduce a functional handle for further coupling.
1. Peptide Analog Synthesis
3-Bromo-D-Phenylalanine is used by peptide chemistry groups to access D-amino acid-containing peptide analogs and peptidomimetic scaffolds where a brominated aromatic side chain is required. The aryl bromide provides a practical functional handle for late-stage diversification, allowing chemists to prepare series of analogs that differ in substitution pattern while maintaining the D-configuration at the amino acid center. This makes the compound useful for custom peptide synthesis and SAR studies where side-chain electronics and steric environment are tuned to evaluate structure-property relationships in peptide-like systems.
2. Medicinal Chemistry SAR Building Block
3-Bromo-D-Phenylalanine supports medicinal chemistry programs that require halogenated aromatic motifs for analog generation, including kinase inhibitor fragments, receptor-binding peptidomimetics, and other small-molecule or hybrid scaffolds derived from amino acid chemistry. The bromine substituent can be leveraged to introduce additional functionality through standard carbon-halogen transformation strategies during library construction, while the D-stereochemistry provides a way to examine stereochemical dependence of binding and selectivity trends in amino-acid-derived pharmacophores. Teams in pharmaceutical intermediate development and medicinal chemistry often choose this reagent because it offers both a defined stereochemical building block and a synthetically useful aryl bromide for iterative design cycles.
3. Chemical Biology Probe Derivatization
3-Bromo-D-Phenylalanine is applied in chemical biology workflows that require amino-acid-based probes bearing a robust aryl halide for subsequent labeling or conjugation chemistry. Researchers use it to incorporate a D-amino acid motif into probe precursors, then use the brominated aromatic handle to enable downstream coupling to other functional groups needed for detection, affinity enrichment, or imaging reagent assembly. This approach is particularly valuable when probe design benefits from stereochemical control and when a stable, non-hydrolyzable aromatic functional handle is preferred during multistep probe construction.
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