3-Bromo-L-tyrosine is a halogenated, naturally occurring aromatic amino acid derivative in which the phenolic side chain of L-tyrosine is substituted with a bromine at the 3-position. The molecule contains a free α-amino group and a free carboxyl group, and it bears a phenolic hydroxyl that remains capable of hydrogen bonding and acid-base behavior while the added bromo substituent provides a chemically addressable handle for further functionalization. In peptide and protein chemistry, it is used as a substrate amino acid for incorporating a brominated tyrosine analogue into peptide sequences for structure-activity studies, site-specific conjugation strategies, and analytical method development where the halogenated aromatic motif can be detected or used for downstream derivatization.
CAT No: CP17601
3-Bromo-L-tyrosine is an L-tyrosine derivative bearing a side-chain phenolic group and a bromo substituent on the aromatic ring, providing a chemically addressable handle for downstream aromatic functionalization while retaining the native tyrosine functionality. This halogenated amino acid is commonly handled as a protected or free building block depending on the supplier grade, and it is valued in peptide and medicinal chemistry workflows where controlled substitution patterns on the tyrosine ring are required. The combination of an aromatic bromide and the phenolic hydroxyl supports selective derivatization strategies that are useful for structure-activity studies, probe synthesis, and targeted intermediate preparation.
1. Peptide Building Block
3-Bromo-L-tyrosine is used as a tyrosine analog building block for preparing peptides and peptide fragments that require a brominated aromatic ring for later diversification or for installing specific substituents at defined positions. Researchers in custom peptide synthesis and peptide library development use this amino acid to generate analog series where aromatic substitution is systematically varied while keeping the tyrosine side-chain functionality consistent with tyrosine-based chemistry. In peptide workflows, the bromo substituent provides a convenient functional handle for subsequent cross-coupling or aromatic modification steps, enabling access to non-natural tyrosine variants that are difficult to obtain from standard tyrosine.
2. Medicinal Chemistry Intermediates
3-Bromo-L-tyrosine serves as a practical intermediate for medicinal chemistry programs that require a brominated phenyl motif derived from tyrosine. Medicinal chemistry groups use it to build substituted aromatic systems for SAR (structure-activity relationship) studies, where the bromide can be leveraged for coupling reactions to install diverse aryl or heteroaryl substituents at the brominated position. The presence of the phenolic hydroxyl also supports downstream derivatization strategies that help modulate physicochemical properties and enable access to protected or functionalized aromatic intermediates used in small-molecule synthesis.
3. Chemical Biology Probe Synthesis
3-Bromo-L-tyrosine is applied in chemical biology for constructing tyrosine-based probes and labeled analogs where controlled aromatic substitution is required to tune reactivity, labeling efficiency, or binding-site mimicry in probe design. Chemical biology and bioconjugation development teams use the brominated aromatic ring as a defined attachment point for subsequent functionalization steps, while the phenolic group supports orthogonal derivatization depending on the probe format. This makes the reagent relevant for workflows that generate aromatic-tagged peptide probes, affinity reagents, or intermediate scaffolds that later undergo coupling to introduce detection or enrichment elements.
4. Analytical Reference Development
3-Bromo-L-tyrosine is also used for analytical method development and reference material preparation in LC-MS and related workflows that require a defined halogenated tyrosine analog. Analytical chemistry teams use it to evaluate chromatographic behavior, retention time windows, and mass spectral characteristics of brominated aromatic amino acid species, supporting identification and quantitation strategies when halogenated tyrosine derivatives are present as standards, metabolites, or synthetic impurities. Because the reagent contains a distinctive brominated aromatic pattern, it provides a useful anchor compound for building calibration or verification sets in targeted analytical panels.
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