3-Iodo-D-tyrosine contains a D-tyrosine amino acid backbone bearing an iodine substituent at the 3-position of the phenolic ring, classifying it as a halogenated, non-proteinogenic tyrosine analogue. The molecule features an α-amino group and a carboxyl group alongside a phenolic side chain that is substituted by iodine, with the stereochemical configuration specified as D. In research and synthetic chemistry, this aryl iodide functionality provides a handle for chemical labeling, conjugation, and incorporation into peptide or small-molecule analogues where halogenated aromatic residues are used for structure-activity studies or analytical method development.
CAT No: CP18702
3-Iodo-D-tyrosine is a D-configured tyrosine analog bearing an iodine substituent at the 3-position of the aromatic ring, providing a stable, heavy-atom handle that is widely exploited in chemical biology and analytical workflows. Its phenolic side chain retains the reactivity typical of tyrosine derivatives, while the aryl iodination enables targeted incorporation into peptides and facilitates detection by mass spectrometry and radiolabeling-compatible chemistry in downstream applications. As a non-proteinogenic amino acid building block, it is commonly used to introduce site-specific iodinated aromatic residues for structural studies, labeling strategies, and quantitative assay development.
1. Peptide Labeling Building Block
3-Iodo-D-tyrosine is used as an iodinated tyrosine building block for custom peptide synthesis, where the 3-iodo aromatic residue provides a defined chemical tag for subsequent detection or derivatization. Researchers incorporate this residue into short peptides and longer peptide conjugates to create well-defined analogs for binding studies, protease recognition experiments, and structure-activity relationship work in medicinal chemistry programs. The D-configuration supports studies that probe stereochemical effects on peptide conformation and enzymatic processing, while the iodinated ring offers a convenient mass shift and a site for further chemical modification without altering the peptide backbone.
2. Chemical Biology Interaction Probes
3-Iodo-D-tyrosine is frequently selected for chemical biology workflows that require an aromatic heavy-atom label to track peptide or protein interactions. In practice, it is incorporated into ligands, peptide probes, or protein fragments to enable analytical readouts by LC-MS workflows and to support mapping experiments where the aromatic iodination serves as a stable chemical marker. Because the phenolic group is present, downstream derivatization strategies can be designed to tune reactivity or conjugation chemistry while maintaining the iodinated aromatic signature for follow-on characterization of labeled species.
3. Analytical Standards And Quantitation
3-Iodo-D-tyrosine is used to prepare analytical reference materials for method development and quantitation, particularly when monitoring iodinated tyrosine-containing species in complex mixtures. Its defined iodination pattern produces characteristic mass spectrometric behavior, making it valuable as a calibration or comparison standard for LC-MS/MS assays that measure tyrosine analogs, iodinated peptide fragments, or labeled biomolecule hydrolysates. Analytical chemists and bioanalytical teams also use this compound to verify chromatographic retention and to support identification workflows that rely on the presence of the 3-iodo aromatic motif.
4. Pharmaceutical Intermediate Development
3-Iodo-D-tyrosine is also used as a specialty intermediate in the synthesis of iodinated aromatic building blocks and peptide-related reagents for research and industrial development. Medicinal chemistry and process development teams leverage the pre-installed 3-iodo aromatic functionality to streamline downstream assembly of iodinated motifs used in SAR libraries, iodinated analog generation, and chemical probe construction. The stable, isolable amino acid form allows controlled incorporation into synthetic sequences where a defined iodinated tyrosine equivalent is required for downstream derivatization and characterization.
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