Boc-3,5-diiodo-Tyr-OSu is a Boc-protected tyrosine derivative bearing two iodine substituents on the aromatic ring and an N-hydroxysuccinimide (OSu) ester at the carboxyl terminus. The molecule contains a Boc-protected amino group, a phenolic side chain characteristic of tyrosine, and the activated OSu ester that presents a leaving group for acyl transfer chemistry while retaining the diiodinated aromatic functionality for spectroscopic and labeling applications. In peptide and bioconjugation workflows, this activated amino acid ester is used as a precursor for introducing a diiodotyrosine residue into larger constructs and for forming amide-linked conjugates with amine-containing targets under controlled coupling conditions.
CAT No: CP26459
CAS No:163679-35-4
Synonyms/Alias:Boc-Tyr(3,5-I2)-OSu;Boc-3,5-diiodo-tyr-osu;163679-35-4;Boc-3,5-diiodo-L-tyrosinehydroxysuccinimideester;15093_ALDRICH;SCHEMBL4450702;15093_FLUKA;C18H20I2N2O7;6242AH;AKOS022181234;ZINC150338770;AK-60143;(S)-2,5-Dioxopyrrolidin-1-yl2-((tert-butoxycarbonyl)amino)-3-(4-hydroxy-3,5-diiodophenyl)propanoate
Boc-3,5-diiodo-Tyr-OSu is a protected tyrosine derivative bearing two iodine atoms on the aromatic ring and an N-Boc backbone protection, with the activated N-hydroxysuccinimide (OSu) ester at the carboxylate. This combination makes it a highly reactive amino acid building block for forming amide bonds under peptide- and bioconjugation-compatible conditions, while the 3,5-diiodo substitution supports radiolabeling and iodine-specific analytical workflows. Researchers and developers commonly select this reagent when they need an iodinated tyrosine unit introduced with controlled stoichiometry and strong coupling efficiency.
1. Iodinated Peptide Coupling
Boc-3,5-diiodo-Tyr-OSu is used as an activated amino acid building block for coupling iodinated tyrosine residues into peptide segments during custom peptide synthesis and medicinal chemistry lead optimization. The OSu ester enables efficient amide bond formation with amine-containing partners, allowing rapid assembly of iodinated peptide intermediates that are otherwise more difficult to introduce using unactivated carboxylic acids. Solid-phase and solution-phase workflows that rely on pre-activated amino acid derivatives often favor this format to improve coupling consistency when the aromatic ring is substituted with 3,5-diiodo groups.
2. Bioconjugation Amide Linkage
Boc-3,5-diiodo-Tyr-OSu is applied in chemical biology and materials research where an iodinated tyrosine motif is required as part of a defined conjugate scaffold. The activated OSu ester supports formation of stable amide linkages to primary amines on peptides, linkers, or biomolecule-derived building blocks, enabling controlled construction of iodinated conjugates for downstream labeling or analytical studies. The N-Boc protection helps maintain reagent integrity during coupling steps, which is particularly useful when preparing amine-reactive conjugation components that must be handled as discrete intermediates.
3. Radiolabeling and Iodine Analytics
Boc-3,5-diiodo-Tyr-OSu is frequently selected for preparing iodinated tyrosine-containing standards and precursors used in iodine-specific analytical development and radiochemistry-adjacent workflows. The 3,5-diiodo substitution provides a chemically defined iodine environment that can be leveraged to generate iodinated peptide or conjugate targets for method development, tracer preparation, or comparative quantification in instrumental analyses. In these settings, the OSu activation supports efficient incorporation of the iodinated residue into the desired framework, reducing variability associated with incomplete coupling that can complicate downstream quantitation.
4. Pharmaceutical Intermediate Development
Boc-3,5-diiodo-Tyr-OSu serves as a specialized intermediate for medicinal chemistry programs that require iodinated aromatic amino acid fragments as part of larger synthetic sequences. Process development teams and custom synthesis groups often use activated amino acid esters like OSu derivatives to streamline the introduction of functionalized tyrosine units into late-stage intermediates, where reproducible coupling and controlled functional group handling are critical. The protected amino acid format supports compatibility with multi-step intermediate synthesis strategies, enabling the iodinated tyrosine motif to be installed with clear stoichiometric control before further elaboration.
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