3-Bromo-DL-tyrosine contains an aromatic phenol-bearing amino acid framework with a bromine substituent at the 3-position of the phenyl ring, classifying it as a halogenated tyrosine derivative in the free amino acid form. It presents a primary amino group and a carboxyl group on the alpha carbon, with the side chain retaining the phenolic hydroxyl functionality that can participate in hydrogen bonding and electrophilic substitution chemistry, while the "DL" designation indicates a racemic mixture of stereoisomers at the alpha center. This compound is used as a substrate for peptide and protein structure-activity studies where tyrosine analogs with a defined aryl halogen handle are required, and it can serve as a precursor for further functionalization such as derivatization of the aromatic bromine for conjugation or analytical labeling workflows.
CAT No: CP17603
3-Bromo-DL-tyrosine is a halogenated tyrosine derivative supplied as a DL (racemic) mixture, featuring a phenolic side chain and a bromine substituent on the aromatic ring. This brominated, unprotected amino acid building block is commonly used when downstream steps require an aryl bromide as a handle for cross-coupling or selective functionalization while retaining the tyrosine phenol for further derivatization. Its dual reactivity makes it a practical intermediate for constructing tyrosine-based motifs in peptide, medicinal chemistry, and materials research workflows.
1. Medicinal Chemistry Intermediates
3-Bromo-DL-tyrosine is frequently used by medicinal chemistry groups to prepare halogenated tyrosine analogs and aryl-substituted building blocks where the aryl bromide enables late-stage diversification. The bromine substituent provides a convenient synthetic handle for coupling reactions that install aryl or heteroaryl groups onto the tyrosine aromatic ring, supporting structure-activity relationship studies that require rapid generation of analog series. Researchers also value the presence of the tyrosine phenolic group as a functional site for additional derivatization or protection strategies during analog synthesis.
2. Peptide And Peptidomimetic Synthesis
3-Bromo-DL-tyrosine is used in custom peptide synthesis and peptidomimetic development when a tyrosine residue bearing an aryl bromide is required as part of a sequence or scaffold. The amino acid functionality supports incorporation as a building block into protected or activated peptide fragments, enabling the brominated aromatic ring to be carried through assembly and then modified later if the target design calls for post-assembly diversification. This approach is particularly useful for generating peptide-based ligands or constrained tyrosine-containing motifs where aryl substitution patterns are tuned after initial peptide construction.
3. Cross-Coupling Functionalization
3-Bromo-DL-tyrosine is widely selected as an electrophilic aromatic intermediate for downstream coupling chemistry, including the formation of biaryl linkages and the introduction of substituted aromatic groups. Synthetic teams use the aryl bromide to connect tyrosine-derived fragments to diverse partners while keeping the amino acid framework available for further conversion into derivatives, conjugation-ready intermediates, or polymerizable units. The combination of an aryl halide with a phenolic side chain supports sequential functionalization strategies commonly used in chemical biology probe development and specialty material precursor preparation.
4. Analytical And Reference Derivative Prep
3-Bromo-DL-tyrosine is also used to prepare analytical standards and reference derivatives for method development where brominated tyrosine motifs serve as chemically defined targets. Laboratories developing LC-MS workflows or monitoring assays for tyrosine-based chemical libraries often rely on brominated intermediates to generate calibration or confirmation compounds that reflect the exact aromatic substitution pattern of interest. In these settings, the stable, well-defined structure of the brominated tyrosine building block helps ensure consistent analytical behavior across synthesis batches and downstream characterization steps.
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