H-3,5-Diiodo-D-Tyr-OH is a D-configured iodinated tyrosine derivative bearing two iodine atoms at the 3 and 5 positions of the aromatic ring, classifying it as a non-proteinogenic, halogenated amino acid. The molecule contains a free carboxylic acid and a free α-amino group and retains a phenolic side chain that can participate in electrophilic aromatic substitution chemistry and undergo typical tyrosine-like derivatization at the hydroxyl. As an isotopically and structurally defined halogenated amino acid analogue, it is used in peptide and small-molecule synthesis where aromatic iodination patterns are required, and in analytical or chemical biology workflows that rely on defined iodine substitution for labeling, conjugation, or structure-activity studies.
H-3,5-Diiodo-D-Tyr-OH is a D-configured iodinated tyrosine derivative bearing two iodine atoms at the 3- and 5-positions of the phenolic ring and a free carboxylic acid and phenolic hydroxyl group. The presence of the stereogenic center at the α-carbon (D-tyrosine configuration) provides defined chirality for downstream peptide coupling and stereochemically controlled incorporation into amino acid sequences. The diiodophenyl motif increases mass and polarizability while retaining the tyrosine phenol as a reactive handle for selective protection, electrophilic substitution, or conjugation chemistry. The free acid and phenol enable standard amino acid activation strategies while supporting derivatization pathways relevant to radiochemical labeling, analytical standards, and chemically defined biomolecule modification.
1. Peptide Synthesis
H-3,5-Diiodo-D-Tyr-OH is used in peptide building block preparation where the amino acid backbone functionality enables coupling to activated carboxyl partners under peptide synthesis conditions. The free carboxylic acid and the D-tyrosine stereocenter support incorporation into linear peptides and peptide fragments with stereochemical fidelity, while the 3,5-diiodo substitution can be retained through protected-amino-acid workflows and later carried forward into iodinated peptide analogs. The phenolic hydroxyl can be protected as an ether or carbonate during chain assembly to prevent side reactions during amide bond formation, then selectively deprotected for native phenol presentation. The resulting iodinated peptide products can be applied in structure-activity relationship studies, binding assays that require defined aromatic substitution patterns, and synthetic libraries where mass-defined tyrosine analogs are needed.
2. Bioconjugation Chemistry
H-3,5-Diiodo-D-Tyr-OH serves as a defined tyrosine-derived conjugation component for biomolecule labeling and chemical biology workflows that require an iodinated aromatic tag. The phenolic hydroxyl provides a functional group for conjugation strategies such as ether formation, linker attachment, or coupling after phenol protection/deprotection cycles, while the carboxyl group can be converted into activated esters or amide-forming intermediates for attachment to proteins, peptides, or polymer backbones. The heavy iodine atoms at the 3,5-positions support mass spectrometric detectability and can be used to generate chemically traceable conjugates with controlled aromatic substitution. The D-configuration can be leveraged when stereochemical control is required for resistance to proteolysis or for matching stereodefined binding motifs in biomolecular assays.
3. Radiolabeling And Imaging Research
H-3,5-Diiodo-D-Tyr-OH is suitable for radiochemistry-oriented research applications where iodinated tyrosine scaffolds are used as precursors for radioiodination and tracer generation. The diiodophenyl arrangement provides a chemically relevant iodine-bearing aromatic system that can participate in labeling workflows or serve as a structural reference when preparing iodinated standards. The intact tyrosine phenol and the carboxylic acid enable conversion into labeling-ready derivatives, supporting downstream incorporation into tracer molecules or iodinated biomolecule fragments. The stereodefined D-tyrosine configuration supports production of stereochemically defined iodinated analogs for analytical comparisons and imaging-relevant chemical studies.
4. Analytical Standards Development
H-3,5-Diiodo-D-Tyr-OH is applied in analytical research as a mass-defined amino acid standard for method development, calibration, and identification of iodinated tyrosine species. The fixed 3,5-diiodo substitution pattern yields characteristic mass and isotopic signatures, while the D-configuration supports unambiguous differentiation from L-tyrosine-derived analogs in chiral separation and targeted mass spectrometry. The free carboxylic acid and phenolic hydroxyl allow consistent derivatization for chromatographic behavior tuning, including protection strategies that can reduce peak tailing or improve ionization reproducibility. The compound can be employed as a reference material in studies quantifying iodinated metabolites, peptide hydrolysates, or iodinated bioconjugates.
5. Pharmaceutical Intermediate Preparation
H-3,5-Diiodo-D-Tyr-OH can function as an amino acid-based intermediate in fine chemical synthesis routes that require iodinated aromatic building blocks for medicinal chemistry and peptidomimetic construction. The combination of a protected-amino-acid-compatible carboxyl group and a phenolic hydroxyl enables transformation into protected derivatives for controlled coupling, including conversion to activated forms for amide formation or esterification for temporary solubility control. The diiodinated aromatic ring can be carried through intermediate steps to preserve iodine substitution patterns that influence molecular recognition, while stereochemical control at the α-carbon supports defined analog series. Downstream use can include preparation of iodinated peptide fragments, tyrosine-based linkers, or stereochemically defined intermediates for manufacturing-oriented synthetic campaigns where reproducible substitution patterns are required.
6. Side-Chain Functionalization
H-3,5-Diiodo-D-Tyr-OH supports side-chain functionalization strategies that exploit the phenolic hydroxyl and the iodinated aromatic ring for controlled chemical modification. Phenol protection and selective deprotection enable orthogonal handling relative to the carboxylic acid, allowing sequential formation of amide or ester linkages while maintaining the aromatic iodine pattern. The diiodinated ring can participate in electrophilic aromatic substitution chemistry under appropriate conditions or serve as a stable, mass-tagged aromatic motif for creating iodinated analogs and conjugation handles. The resulting functionalized derivatives can be used to generate peptidomimetics, enzyme-substrate analogs, or chemically defined materials where a tyrosine-like aromatic unit with preserved stereochemistry is required.
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