Boc-3,5-Diiodo-D-tyrosine is a Boc-protected, halogenated tyrosine derivative in which the tyrosine aromatic ring bears two iodine atoms at the 3- and 5-positions and the amino acid backbone is present in the D stereochemical form as indicated by the product name. The molecule contains a Boc-protected α-amino group and a free carboxyl group, while its phenolic side chain remains available for chemical handling and the heavy halogens provide distinct mass and electron-withdrawing character for analytical and conjugation workflows. In synthesis, this protected amino acid is used as a precursor for introducing iodinated tyrosine analogues into peptide or peptide-like constructs and for preparing labeled or traceable aromatic side chains for structure-activity studies, molecular labeling, or bioconjugation chemistry.
CAT No: CP02156
CAS No:214630-08-7
Synonyms/Alias:Boc-3,5-Diiodo-D-tyrosine;214630-08-7;CHEMBL310394;C14H17I2NO5;AC1MHO4O;2-tert-Butoxycarbonylamino-3-(4-hydroxy-3,5-diiodo-phenyl)-propionicacid;Boc-D-Tyr(3,5-I2)-OH;CTK8E5710;MolPort-006-705-796;7284AD;BDBM50145825;ZINC26503091;AKOS015836536;AM82354;RTR-010080;KB-48191;TR-010080;FT-0679830;K-6140;I14-26482;(2R)-2-(tert-butoxycarbonylamino)-3-(4-hydroxy-3,5-diiodo-phenyl)propanoicacid;(2R)-2-[(tert-butoxycarbonyl)amino]-3-(4-hydroxy-3,5-diiodophenyl)propanoicacid;(R)-2-tert-Butoxycarbonylamino-3-(4-hydroxy-3,5-diiodo-phenyl)-propionicacid;(2R)-3-(4-hydroxy-3,5-diiodophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoicacid
Boc-3,5-Diiodo-D-tyrosine is a protected D-tyrosine derivative bearing two iodine atoms on the aromatic ring (3,5-diiodo substitution) and an N-terminal Boc protecting group. This halogenated tyrosine building block is widely used in peptide and small-molecule synthesis where radioiodination-like or iodine-rich aromatic chemistry is required, and the Boc group supports controlled coupling during protected-amino-acid assembly. The D stereochemistry and the diiodophenyl side-chain make it particularly relevant for thyroid-hormone motif analogs and iodine-dependent structural or labeling strategies in chemical biology workflows.
1. Iodinated Peptide Building Blocks
Boc-3,5-Diiodo-D-tyrosine is used as an iodinated amino acid building block for constructing peptides that incorporate a 3,5-diiodotyrosine motif, including hormone-mimetic sequences and iodine-rich peptide standards. Peptide synthesis groups and custom peptide manufacturers rely on the Boc-protected amino acid form to enable stepwise assembly while preserving the diiodophenyl substitution through downstream handling. The aromatic iodine pattern provides a dense, chemically distinctive side chain that supports downstream analytical readouts and structure-specific studies, while the D configuration offers stereochemical control for designing analogs that probe backbone or side-chain stereochemical effects.
2. Chemical Biology Thyroid-Motif Analogues
Boc-3,5-Diiodo-D-tyrosine is frequently selected for chemical biology projects that develop thyroid-motif analogues, including probes and peptide reagents used to investigate iodine-dependent recognition, processing, or binding behaviors in vitro. Researchers in protein chemistry and biomolecular interaction studies use this building block to introduce a defined diiodotyrosine element into synthetic constructs, enabling motif-specific comparisons against mono-iodinated or non-iodinated controls. The combination of Boc protection and the stable diiodophenyl aromatic substitution supports consistent incorporation into synthetic ligands used for binding assays, competitive studies, and mechanistic experiments that require a chemically defined iodine-bearing residue.
3. Analytical Standards And LC-MS Targets
Boc-3,5-Diiodo-D-tyrosine is used to prepare defined iodinated peptide or amino acid reference materials for analytical method development and targeted mass spectrometry workflows. Analytical chemists and proteomics/metabolomics groups often value this type of diiodinated residue because it generates strong, readily trackable mass signatures and supports unambiguous identification of motif-containing analytes in LC-MS/MS experiments. The protected form also helps researchers standardize synthetic inputs when building calibration or qualification compounds, ensuring that the iodine substitution pattern and stereochemistry are consistent across standard batches.
4. Pharmaceutical Intermediate Development
Boc-3,5-Diiodo-D-tyrosine is applied as a specialized pharmaceutical-intermediate building block in the synthesis of iodinated aromatic fragments and peptide-like intermediates used in medicinal chemistry programs. Process development teams and synthetic chemistry groups incorporate this protected, diiodinated tyrosine derivative when a controlled introduction of a 3,5-diiodoaryl motif is required for SAR studies, stereochemical analog generation, or downstream coupling into larger scaffolds. The Boc-protected amino functionality supports reliable intermediate formation and handling during multi-step synthesis, while the diiodophenyl side chain provides a chemically distinctive handle for subsequent derivatization strategies used in research compound manufacturing.
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