3,5-Dibromo-D-tyrosin is a halogenated, non-natural amino acid derivative in the tyrosine family, bearing a phenolic aromatic side chain substituted with two bromine atoms at the 3 and 5 positions and featuring a D-configured α-amino acid backbone. The molecule contains an α-amino group and a carboxylic acid group, and the brominated phenol provides a distinct electron-withdrawing, heavier-atom substituted aromatic functionality that can support chemical labeling, conjugation, or spectroscopic contrast relative to unmodified tyrosine. In synthetic and analytical workflows, this dibrominated tyrosine analogue is used to prepare modified peptides and protein fragments containing halogenated aromatic residues, and it can serve as a precursor for further derivatization of the phenolic ring for structure-activity studies, crosslinking handle introduction, or isotope-independent detection strategies.
CAT No: CP02151
CAS No:50299-42-8
Synonyms/Alias:3,5-Dibromo-D-tyrosine;50299-42-8;(R)-2-Amino-3-(3,5-dibromo-4-hydroxyphenyl)propanoicacid;C9H9Br2NO3;AC1LEM45;SCHEMBL838919;CTK8F4829;H-D-Tyr(3,5-Br2)-OH;ZINC57300;MolPort-020-004-219;CS-M0465;3220AH;AKOS022186472;AM83554;AJ-09658;AK144764;KB-28545;DB-022009;K-9314;(2R)-2-amino-3-(3,5-dibromo-4-hydroxyphenyl)propanoicacid
3,5-Dibromo-D-tyrosin is a halogenated D-tyrosine derivative bearing two bromine atoms on the aromatic ring, providing a distinctive electronic and steric profile while retaining the tyrosine side-chain functionality for downstream derivatization. This amino acid building block is commonly used in peptide and chemical biology workflows where controlled aromatic substitution is required, including applications that benefit from the presence of heavy halogens for analytical discrimination and for tailoring reactivity during synthesis. The D-configuration supports use in stereochemically defined peptide constructs and non-natural amino acid incorporation strategies.
1. Peptide Building Block
3,5-Dibromo-D-tyrosin is used as an aromatic, halogenated amino acid building block for peptide synthesis projects that require stereodefined tyrosine analogs. Researchers incorporate this residue into custom peptides to probe structure-property relationships, including how ring substitution and heavy-atom content influence peptide conformation, stability during chemical handling, and analytical readouts. In practice, it is selected when the experimental design calls for a tyrosine-like side chain with a specifically substituted phenyl ring rather than an unsubstituted phenolic aromatic.
2. Chemical Biology Probes
3,5-Dibromo-D-tyrosin supports chemical biology and molecular probe construction where a tyrosine-derived aromatic motif is needed as a defined chemical handle. The dibrominated ring is often leveraged to create probes that can be tracked by mass spectrometry with improved mass discrimination and to enable downstream functionalization strategies that depend on the substituted aromatic platform. Teams developing ligand analogs, receptor-binding probes, or peptide-based chemical probes use this building block to introduce a stereochemically controlled, halogen-rich aromatic element into their probe scaffolds.
3. Pharmaceutical Intermediate Development
3,5-Dibromo-D-tyrosin is also employed as a specialty intermediate for medicinal chemistry and process development programs that require a halogenated tyrosine-derived motif. Organic synthesis teams use it to access substituted aromatic fragments for constructing larger heterocycles, aryl linkers, or tyrosine-mimetic scaffolds used in lead optimization campaigns. The two bromine substituents provide a practical starting point for further aromatic transformations in industrial and research settings where controlled substitution patterns are critical for SAR (structure-activity relationship) exploration and final scaffold assembly.
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