Boc-3,5-diiodo-Tyr-OMe is a Boc-protected tyrosine derivative in which the phenolic ring bears two iodine substituents at the 3- and 5-positions and the carboxyl group is present as a methyl ester (Tyr-OMe). The molecule contains a Boc-protected amino functionality and an O-methyl ester, while the iodinated aromatic side chain retains a phenolic oxygen that can participate in electrophilic aromatic substitution-type chemistry or serve as a site for further functionalization, with stereochemistry not specified in the name. In peptide and labeling workflows, this protected, halogenated amino acid ester is used as a precursor for incorporating an iodinated tyrosine residue into synthetic sequences and for preparing radioisotope-free or chemically traceable aromatic motifs for analytical method development and structure-activity studies.
CAT No: CP26290
CAS No:128781-80-6
Synonyms/Alias:BOC-3,5-DIIODO-TYR-OME;128781-80-6;SCHEMBL5123861;C15H19I2NO5;CTK8B4810;LYSAEUWOAILRMR-NSHDSACASA-N;6241AH;ZINC71788016;N-t-butoxycarbonyl-3,5-diiodo-L-tyrosinemethylester;3,5-Diiodo-N-(tert-butoxycarbonyl)-L-tyrosinemethylester
Boc-3,5-diiodo-Tyr-OMe is a protected iodinated tyrosine derivative featuring a Boc-protected amino group, a methyl ester (OMe) on the carboxyl terminus, and two iodine atoms on the aromatic ring at the 3 and 5 positions. This combination makes it a practical aromatic halogenated building block for constructing tyrosine-containing peptide segments and for preparing iodinated intermediates used in chemical biology and radiolabeling workflows. The presence of the protected termini supports downstream coupling strategies in peptide synthesis, while the diiodo substitution pattern is commonly leveraged for controlled reactivity and analytical traceability.
1. Iodinated Peptide Segment Synthesis
Boc-3,5-diiodo-Tyr-OMe is used by peptide chemistry groups and custom peptide manufacturing teams as an iodinated tyrosine building block for assembling peptide segments that require a diiodophenyl motif. The Boc protection on the amino functionality and the methyl ester on the carboxyl side provide a defined synthetic handle for stepwise coupling during protected-amino-acid peptide assembly. Researchers select this specific diiodo substitution pattern when they need tyrosine-derived aromatic iodination to support subsequent labeling, conjugation, or downstream derivatization while maintaining the integrity of the aromatic substitution pattern during peptide construction.
2. Radiolabeling and Iodination Precursors
Boc-3,5-diiodo-Tyr-OMe is commonly positioned as a chemical intermediate for workflows that rely on iodine chemistry, including preparation of iodinated aromatic motifs used in radiolabeling development and tracer-oriented synthesis. The 3,5-diiodo substitution pattern is particularly relevant for downstream transformations where iodine atoms on the phenyl ring are treated as functional elements that can be exchanged, retained, or leveraged for controlled labeling strategies. Medicinal chemistry and chemical biology laboratories often use such iodinated tyrosine derivatives to generate defined iodinated analogs for assay development, tracer screening, and analytical method optimization.
3. Aromatic Halogenated Intermediate Development
Boc-3,5-diiodo-Tyr-OMe is used as a stable, protected precursor for producing a range of aromatic halogenated intermediates where the diiodo tyrosine scaffold must be carried through multi-step synthesis without premature functional group interference. The protected amino group and esterified carboxyl terminus help maintain chemoselectivity during intermediate elaboration, enabling conversion into downstream derivatives used in chemical biology reagent development and specialty intermediate manufacturing. Process and development chemists value this form when they need a well-defined iodinated scaffold that can be further functionalized while preserving the 3,5-diiodo aromatic pattern.
4. Analytical Reference and LC-MS Method Support
Boc-3,5-diiodo-Tyr-OMe is also used in analytical chemistry workflows as a defined iodinated tyrosine derivative for method development and reference material preparation. Laboratories developing LC-MS or related analytical assays for iodinated aromatic compounds often require chemically characterized standards that reflect the exact substitution pattern and protected functionality present in their target analytes or intermediates. By providing a consistent diiodo aromatic signature alongside protected termini, this compound supports verification of retention behavior, ionization characteristics, and identity confirmation during method qualification for iodinated peptide-related samples and intermediate mixtures.
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