3,5-Dibromo-DL-tyrosine is a halogenated, non-proteinogenic tyrosine derivative in which the phenolic side chain of tyrosine is substituted with bromine atoms at the 3 and 5 positions, yielding a substituted aromatic amino acid bearing an amino group and a carboxyl group. The molecule contains the phenolic hydroxyl functionality on the ring, and the "DL" designation indicates a racemic mixture with both stereoisomeric forms at the alpha carbon, while the side chain remains capable of participating in hydrogen bonding and electrophilic substitution chemistry typical of halogenated phenols. In synthesis and analytical workflows, this dibrominated amino acid is used as a precursor for preparing halogenated peptide analogues and for introducing brominated aromatic motifs into peptide building blocks, as well as for structure-activity and labeling studies where controlled aromatic substitution patterns are required.
CAT No: CP17903
3,5-Dibromo-DL-tyrosine is a halogenated tyrosine analog supplied as a DL (racemic) mixture, featuring two bromine atoms on the phenolic ring that strongly influence aromatic reactivity and mass spectrometric detectability. As an amino acid building block with a free phenolic hydroxyl and an amino acid backbone, it is frequently selected for radiolabeling workflows, halogen-controlled derivatization, and as a chemically defined reference material in analytical or synthetic chemistry where tyrosine-like functionality is required.
1. Radiolabeling Precursor Development
3,5-Dibromo-DL-tyrosine is used as a practical precursor in radiochemistry and tracer development workflows that rely on tyrosine-derived aromatic halogenation patterns. Researchers in chemical biology, radiopharmaceutical research, and analytical tracer production use this dibrominated scaffold to access downstream iodination or related halogen-exchange strategies that generate labeled aromatic tyrosine analogs for binding, uptake, or distribution studies in chemical systems. The presence of two bromines on the phenolic ring provides a defined starting halogen pattern that supports consistent downstream labeling chemistry, while the free amino acid functionality enables integration into multistep tracer synthesis plans.
2. Halogenated Aromatic Derivative Synthesis
3,5-Dibromo-DL-tyrosine serves as a robust intermediate for preparing halogen-rich tyrosine derivatives used in structure-property investigations and specialized medicinal chemistry programs. Medicinal chemistry groups and custom synthesis providers leverage the dibrominated phenolic ring to tune reactivity for subsequent functionalization, including electrophilic aromatic substitution and coupling-based derivatization routes that build toward iodinated, substituted, or cross-coupled aromatic motifs. The tyrosine backbone and phenolic hydroxyl support further derivatization while maintaining a recognizable amino acid handle for downstream conversion into protected intermediates or conjugatable forms.
3. Analytical Reference And Mass Spec Standards
3,5-Dibromo-DL-tyrosine is commonly used to support analytical method development and calibration/qualification work where a defined halogenated tyrosine species is required. Because the compound contains two bromine atoms, it produces characteristic isotope-containing mass signatures that are valuable for LC-MS and related quantitative or confirmatory workflows, including stability checks of derivatized tyrosine analogs and verification of labeling or halogenation outcomes. Analytical laboratories and method-development teams use this reagent as a chemically characterized reference to improve traceability when monitoring tyrosine-like compounds and their halogenated derivatives in complex matrices.
4. Peptide And Conjugate Building Block
3,5-Dibromo-DL-tyrosine is applied as an amino acid building block for preparing halogenated tyrosine-containing peptides and peptide-like conjugates used in chemical biology and materials-oriented studies. Peptide synthesis teams incorporate this dibrominated tyrosine analog into custom sequences when a tyrosine-derived aromatic motif with enhanced labeling or derivatization potential is required for downstream experiments. The free phenolic hydroxyl and amino acid functionality allow it to be positioned for conversion into protected coupling-ready forms or for incorporation into defined conjugation strategies, enabling controlled introduction of halogenated aromatic groups into larger biomolecular constructs.
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