Boc-3,5-diiodo-Tyr(2,6-dichloro-Bzl)-OH is a protected tyrosine derivative bearing a Boc-protected amino group and a carboxylic acid functionality, with a phenolic aromatic side chain substituted by iodine atoms at the 3 and 5 positions. The tyrosine phenolic oxygen is benzylated with a 2,6-dichlorobenzyl protecting group, and the molecule contains an additional benzyl ether linkage that modulates phenol reactivity during peptide assembly. As an amino acid building block for peptide synthesis and related structure-activity studies, the halogenated aromatic pattern and protected phenol provide handles for controlled deprotection and subsequent incorporation into peptide frameworks for analytical labeling, crosslinking-compatible designs, or chemical biology workflows.
CAT No: CP26712
CAS No:201416-66-2
Synonyms/Alias:201416-66-2;BOC-3,5-DIIODO-TYR(2',6'-DICHLORO-BZL)-OH;C21H21Cl2I2NO5;SCHEMBL9162903;BOC-3,5-DIIODO-TYR-OH;6239AH;ZINC150338815;Boc-3,5-diiodo-Tyr(2,6-dichloro-Bzl)-OH;K-5893
Boc-3,5-diiodo-Tyr(2,6-dichloro-Bzl)-OH is a Boc-protected iodinated tyrosine derivative bearing a 2,6-dichlorobenzyl side-chain protecting group, designed for peptide and peptide-conjugate synthesis where the aromatic iodines and tyrosine phenol are preserved through protected-handling strategies. The combination of Boc on the amino terminus and benzyl protection on the phenolic oxygen supports controlled deprotection during downstream assembly, while the diiodo substitution pattern provides a chemically distinctive handle for radiolabeling workflows and iodine-specific analytical or derivatization steps. This reagent is therefore used by peptide chemists and chemical biology teams to access tyrosine-containing intermediates that carry iodine functionality into larger constructs.
1. Peptide Synthesis Building Block
Boc-3,5-diiodo-Tyr(2,6-dichloro-Bzl)-OH is used as a protected tyrosine building block for custom peptide synthesis workflows where incorporation of an iodinated aromatic residue is required. Peptide synthesis groups rely on the Boc-protected amino functionality to integrate the residue into segment condensation or automated peptide assembly strategies, while the 2,6-dichlorobenzyl protection helps maintain the tyrosine phenolic oxygen during coupling and purification steps. This product is particularly relevant for preparing iodinated peptide segments that later undergo selective deprotection and further functionalization, enabling consistent residue placement in peptide libraries and sequence-defined analogs.
2. Radiolabeling-Ready Tyrosine Residue
Boc-3,5-diiodo-Tyr(2,6-dichloro-Bzl)-OH supports development programs that require iodine-rich tyrosine motifs as precursors for radioiodination and iodine-specific labeling strategies. Researchers in radiochemistry and chemical biology often choose iodinated tyrosine derivatives because the diiodo substitution pattern provides a direct pathway to introduce radioisotopes onto aromatic rings after the protected intermediate is incorporated into a peptide or scaffold. In practice, the protected form helps keep the iodine functionality intact through peptide assembly and purification, so downstream labeling can be performed on a well-defined, sequence-controlled precursor rather than on a heterogeneous mixture of unprotected iodinated species.
3. Iodinated Peptide Conjugates
Boc-3,5-diiodo-Tyr(2,6-dichloro-Bzl)-OH is applied in the preparation of iodinated peptide conjugates used as chemical biology tools and analytical reagents. Teams building peptide-based probes or linker-containing constructs often need an iodinated tyrosine residue to serve as a stable, chemically defined aromatic platform for later derivatization or tag installation, while the Boc and 2,6-dichlorobenzyl protections enable assembly under conditions that would otherwise risk phenolic side reactions. By delivering the iodinated tyrosine in a protected, coupling-ready form, the reagent supports reproducible downstream conjugation workflows where residue integrity and sequence specificity are critical.
4. Analytical Reference and Derivatization
Boc-3,5-diiodo-Tyr(2,6-dichloro-Bzl)-OH is also used to generate iodinated tyrosine-containing standards and derivatization reagents for analytical method development. Analytical chemistry groups commonly require structurally defined iodinated amino acid or peptide fragments to verify chromatographic behavior, confirm identity by mass spectrometry, and support method qualification for iodine-tagged compounds. The protected intermediate format helps ensure that the reagent can be handled and incorporated into defined reference constructs, improving reproducibility when preparing calibration or control materials that contain an iodinated tyrosine motif.
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