Boc-3,5-Diiodo-L-tyrosine ethyl ester is a protected, iodinated tyrosine derivative in which the phenolic side chain of L-tyrosine bears two iodine substituents at the 3 and 5 positions, and the carboxyl group is converted to an ethyl ester. The molecule contains a Boc-protected amino group (tert-butoxycarbonyl) that masks the primary amine, while retaining the esterified carboxyl functionality and the heavily halogenated phenolic ring that supports radioisotope- or heavy-atom-based labeling and spectroscopic contrast. As a stepwise peptide-synthesis intermediate, it provides a protected amino acid building block for incorporating diiodotyrosine residues into peptide sequences and for preparing analytical or chemical biology probes where the diiodinated aromatic motif serves as a defined functional handle.
CAT No: CP02157
Boc-3,5-Diiodo-L-tyrosine ethyl ester is a protected iodinated tyrosine derivative designed for downstream peptide and radiochemistry-adjacent workflows. The L-tyrosine core bears two iodine atoms on the aromatic ring, enabling strong mass/elemental contrast for analytical tracking and providing a chemically informative aromatic handle, while the Boc group and ethyl ester protect the amino acid functionality during synthesis. This reagent is commonly selected by peptide chemists and medicinal chemistry teams when they need an iodinated tyrosine building block that can be assembled into defined sequences or used as a controlled intermediate for further functionalization.
1. Iodinated Peptide Building Blocks
Boc-3,5-Diiodo-L-tyrosine ethyl ester is used as an iodinated tyrosine building block for custom peptide synthesis where aromatic iodination is required to introduce elemental labels, to support downstream derivatization, or to create defined "iodotyrosine" motifs in peptide constructs. Research groups in peptide chemistry and chemical biology often incorporate this residue into peptide segments to generate sequence-defined materials for binding studies, structure-activity relationship (SAR) investigations, or receptor/ligand mapping workflows that rely on the presence of iodine atoms for analytical readouts. The Boc protection and ethyl ester form help maintain the amino acid functionality during coupling steps, supporting reliable incorporation into protected peptide intermediates prior to final deprotection and workup.
2. Medicinal Chemistry Radio/Label Intermediates
Boc-3,5-Diiodo-L-tyrosine ethyl ester is frequently handled as a medicinal chemistry intermediate when iodinated aromatic residues are needed for tracer-like chemistry or for preparing well-defined iodinated motifs used in exploratory labeling strategies. Teams developing iodinated compounds for mechanistic studies or analytical standards value the reagent's defined 3,5-diiodo substitution pattern, which provides a consistent elemental signature for LC-MS and related mass-based workflows. In practice, chemists use this compound to build controlled intermediates that can be carried forward into larger molecules, including peptide-small molecule conjugates and iodinated aromatic fragments, where the stereochemically defined tyrosine scaffold and protected functional groups simplify stepwise assembly.
3. Analytical Standards And Mass Contrast
Boc-3,5-Diiodo-L-tyrosine ethyl ester is also used to prepare analytical reference materials and method-development standards that benefit from the high atomic mass and distinctive isotopic pattern of iodine. Analytical chemistry laboratories use iodinated tyrosine derivatives to validate extraction, chromatography behavior, and mass spectrometric detection for workflows that monitor iodinated aromatic species, including peptide-related LC-MS methods. The protected Boc/ethyl-ester form is particularly useful when the goal is to standardize a specific synthetic stage or chemical form rather than relying on a more reactive free amino acid, enabling consistent handling during calibration, system suitability checks, and comparative quantitation experiments.
4. Tyrosine-Based Conjugate Precursors
Boc-3,5-Diiodo-L-tyrosine ethyl ester serves as a practical precursor for tyrosine-derived conjugation strategies where the aromatic iodines must be preserved through early stages of synthesis. Chemical biology and biomaterials researchers often require defined iodinated aromatic residues to generate conjugates with controlled composition, such as iodinated peptide fragments used in immobilization schemes or as defined components in multistep assembly of larger constructs. By maintaining protected amino and ester functionalities during intermediate preparation, this reagent supports reproducible downstream coupling or transformation steps while keeping the 3,5-diiodo aromatic substitution intact for the intended analytical or functional role.
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