Boc-3,5-Dibromo-D-tyrosine is a protected, halogenated derivative of the amino acid tyrosine, featuring a benzyl side chain with two bromine substituents at the 3 and 5 positions and a D-stereochemical configuration as indicated by the name. The molecule contains an N-terminal Boc (tert-butoxycarbonyl) protecting group on the amino functionality and an unprotected carboxylic acid, with the phenolic side-chain hydroxyl retained as part of the tyrosine scaffold to provide a polar handle for further chemical manipulation or conjugation chemistry. In peptide synthesis workflows, the Boc protection supports chemoselective handling of the amino group during stepwise assembly, while the dibromo aromatic pattern provides a chemically addressable site for structure-activity studies, radiolabeling or halogen-based derivatization strategies, and analytical method development involving halogenated aromatic amino acid residues.
CAT No: CP02153
CAS No:204692-75-1
Synonyms/Alias:Boc-3,5-Dibromo-D-tyrosine;204692-75-1;BOC-D-TYR(3,5-BR2)-OH;C14H17Br2NO5;SCHEMBL3956664;CTK8E5709;FIKNCGRWSBGBKP-SNVBAGLBSA-N;MolPort-020-004-174;ZINC2569781;6238AH;AM82352;KB-48186;RT-011686;K-5972;N-[(1,1-dimethylethoxy)-carbonyl]-3,5-dibromo-D-tyrosine
Boc-3,5-Dibromo-D-tyrosine is a D-tyrosine derivative bearing two bromine atoms on the aromatic ring and a Boc protecting group on the amino functionality, providing a halogenated, protected amino acid building block for peptide and medicinal chemistry synthesis. The dibromo substitution pattern supports downstream electrophilic aromatic functionalization and radio/halogen chemistry workflows, while the D-configuration enables access to stereochemically defined peptidomimetic and non-natural peptide architectures. As a Boc-protected amino acid, it is commonly handled as a protected intermediate for controlled incorporation into larger synthetic sequences.
1. Peptidomimetic Building Blocks
Boc-3,5-Dibromo-D-tyrosine is used by peptide chemistry groups to assemble non-natural peptide segments where a halogenated tyrosine analogue is required for structural probing, conformational effects, or synthetic handle introduction. The protected Boc amino group supports stepwise peptide assembly workflows, while the 3,5-dibromo aromatic pattern provides a chemically distinct phenyl ring compared with native tyrosine, enabling tailored downstream derivatization after peptide assembly or during segment elaboration. Researchers developing D-amino acid-containing peptides frequently select this building block to introduce stereochemical inversion at the residue level while maintaining a tyrosine-like aromatic side chain for subsequent functionalization strategies.
2. Medicinal Chemistry Intermediates
Boc-3,5-Dibromo-D-tyrosine is also applied in medicinal chemistry and SAR-driven synthesis programs as a halogenated aromatic amino acid intermediate. The dibromo substitution at the 3,5-positions is particularly useful when a synthetic route needs a defined, highly substituted phenyl precursor that can be transformed into other aryl motifs through standard cross-coupling or substitution strategies. Development chemists use this reagent to access tyrosine-derived fragments that maintain an amino acid-derived scaffold while enabling rapid diversification of the aromatic ring for library synthesis, lead optimization, and the preparation of analogs used in structure-property studies.
3. Halogenated Aromatic Derivatization
Boc-3,5-Dibromo-D-tyrosine serves as a practical starting material for workflows that require a protected, halogen-rich aromatic platform for later derivatization. The presence of two bromines on the phenyl ring provides multiple sites for selective transformation, allowing chemists to tune aromatic substitution patterns while retaining the amino acid framework for further coupling or conversion to other protected/activated derivatives. In chemical biology and materials-oriented synthesis, this type of dibrominated tyrosine analogue is often selected to introduce a robust, pre-functionalized aromatic handle that can be carried through intermediate stages and then converted to the desired aryl functionality at a controlled step.
4. Stereodefined Non-Natural Residues
Boc-3,5-Dibromo-D-tyrosine is used to prepare stereochemically defined non-natural residues for studies that require D-amino acid incorporation rather than the proteinogenic L configuration. Peptide and peptidomimetic developers rely on D-residue building blocks to generate well-defined stereochemical outcomes in synthetic libraries and to support structure-focused comparisons across residue variants. The combination of D-configuration with a Boc-protected amino group and a dibrominated tyrosine aromatic side chain makes it a convenient choice for constructing residue-specific analog series where both stereochemistry and aromatic substitution pattern are controlled parameters in downstream evaluation workflows.
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