3-Bromo-D-tyrosine is a halogenated, non-proteinogenic amino acid derivative of the tyrosine family bearing a bromine substituent at the 3-position of the phenolic ring and a D-stereochemical configuration at the α-carbon. The molecule contains a free α-amino group and a free carboxyl group, along with a phenolic hydroxyl that can participate in hydrogen bonding and electrophilic substitution at the aromatic ring, while the C-Br bond provides a chemically addressable handle for further derivatization. In synthetic and chemical biology workflows, it is used as a substrate-like building block for preparing modified peptides and as a labeled or reactive aromatic intermediate for conjugation, crosslinking, and structure-activity studies where controlled aromatic substitution is required.
CAT No: CP17602
3-Bromo-D-tyrosine is a D-configured tyrosine analog bearing a bromine substituent on the aromatic ring, providing a site-selective handle for downstream derivatization and controlled incorporation into peptide and small-molecule frameworks. The phenolic side chain supports standard tyrosine chemistry, while the aryl bromide enables coupling strategies that are commonly used to build halogenated aromatic motifs, generate substituted tyrosine derivatives, or introduce functional groups at a defined position. This combination makes 3-bromo-D-tyrosine a useful research-grade building block for stereochemically defined, non-proteinogenic aromatic amino acid design.
1. Halogenated Peptide Building Blocks
3-Bromo-D-tyrosine is used by peptide chemistry groups to construct D-amino acid-containing peptide segments where the aromatic bromine provides a defined substitution pattern on the tyrosine ring. Researchers commonly employ it in custom peptide synthesis workflows to access halogenated tyrosine analogs for structure-activity relationship studies, protease/peptidase substrate profiling, or conformational and aromatic interaction tuning in non-natural peptide libraries. The D-configuration supports stereochemical control for experiments that compare L- versus D-amino acid behavior in peptide assemblies, while the phenolic side chain allows further downstream functionalization or derivatization after peptide assembly.
2. Aromatic Functionalization Via Coupling
3-Bromo-D-tyrosine is selected by medicinal chemistry and chemical biology teams as an intermediate building block for installing additional substituents onto the tyrosine aromatic ring using the aryl bromide as a reactive coupling site. In practical small-molecule and peptidomimetic development, the brominated aromatic motif helps enable rapid diversification toward substituted phenyl/heteroaryl derivatives while retaining the tyrosine backbone features needed for consistent scaffold comparison. This approach is particularly valuable when a defined positional relationship between the phenolic functionality and the newly introduced aromatic group is required for binding studies, SAR mapping, or generation of analog series.
3. Chemical Biology Probe Precursors
3-Bromo-D-tyrosine is used as a stereochemically defined precursor for chemical biology workflows that require tyrosine-derived aromatic probes with a functional handle for later conjugation or labeling. Chemical biology researchers can leverage the brominated ring to introduce probe-specific substituents through coupling chemistry, then use the phenolic group to guide subsequent derivatization steps tailored to the target assay format. The D-tyrosine framework is especially useful when probe stability or stereochemical selectivity is a design consideration for studying protein interactions, affinity reagents, or aromatic recognition motifs in controlled experimental systems.
4. Pharmaceutical Intermediate Development
3-Bromo-D-tyrosine is employed in industrial and development settings as a chiral amino acid intermediate for manufacturing substituted tyrosine analogs and related building blocks used in downstream synthesis of peptidomimetic and aromatic-rich scaffolds. Process and R&D chemists value the combination of a tyrosine-compatible side chain and an aryl bromide handle because it supports modular route planning: the bromine enables late-stage aromatic diversification, while the preserved amino acid functionality supports incorporation into larger intermediates. This makes 3-bromo-D-tyrosine a practical starting material when a defined halogenated aromatic pattern and stereochemical control are required for intermediate libraries and custom synthesis campaigns.
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