3-Iodo-DL-tyrosine contains the phenolic amino acid framework of tyrosine with an iodine substituent at the 3-position of the aromatic ring, and it is supplied as the DL (racemic) stereochemical form. The molecule bears a free α-amino group and a free carboxyl group alongside a phenolic hydroxyl that can participate in hydrogen bonding and electrophilic aromatic substitution at the ring under appropriate conditions. In biochemical and synthetic workflows, this iodinated tyrosine analogue is used as a structurally defined precursor for preparing iodinated peptide or protein fragments and for analytical labeling approaches where an aryl iodide functional handle is required.
CAT No: CP18703
3-Iodo-DL-tyrosine is an iodinated tyrosine analog supplied in the DL (racemic) stereochemical form, featuring the phenolic side chain characteristic of tyrosine together with a reactive aryl iodide at the 3-position. This halogenated aromatic amino acid is widely used as a structural and functional building block for incorporating iodine into peptide and small-molecule frameworks, and for downstream derivatization where the iodide serves as a handle for coupling or radio/labeling strategies in research workflows. As a non-proteinogenic, halogen-substituted amino acid, it is typically handled as a specialized reagent for synthesis and analytical method development rather than as a directly incorporated biological nutrient.
1. Iodinated Peptide Building Block
3-Iodo-DL-tyrosine is used by peptide chemistry groups to introduce an iodine-bearing tyrosine residue into custom peptides and peptide libraries, enabling structure-property studies and site-specific aromatic substitution patterns. Researchers commonly select this amino acid when they need a tyrosine-like phenolic functionality while also installing an aryl iodide at the 3-position for subsequent functionalization or for generating defined iodinated analogs for binding, stability, or conformational studies. In practical peptide synthesis workflows, it serves as a specialty amino acid building block for preparing iodinated peptide standards and reference materials used in analytical characterization and method validation.
2. Radioiodination and Labeling Research
3-Iodo-DL-tyrosine is frequently employed in chemical biology and tracer chemistry workflows where iodinated aromatic substrates are required for radiolabeling or iodide-based tagging strategies during research development. The presence of the 3-iodo substituent provides a convenient starting point for studies that compare iodinated tyrosine analogs, evaluate labeling efficiency in assay development, or generate defined iodinated species for downstream chromatographic and mass spectrometric analysis. Because this reagent is supplied as a DL mixture, it is typically chosen for labeling and analytical method development where stereochemical purity is not the primary requirement, such as preparing comparative standards or calibrants.
3. Coupling and Aromatic Functionalization
3-Iodo-DL-tyrosine is used as an iodinated aromatic intermediate for synthetic diversification, where the aryl iodide enables coupling chemistry to install additional substituents on the tyrosine ring system. Medicinal chemistry and process development teams often incorporate this type of halogenated amino acid into intermediate sequences to access iodinated-to-substituted analogs with defined substitution patterns, supporting structure-activity relationship studies and analog generation. The tyrosine phenolic functionality further supports orthogonal downstream derivatization strategies in small-molecule and peptide-small-molecule conjugate synthesis, making the reagent a practical platform for building iodinated aromatic motifs with controlled substitution.
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