H-3,5-Diiodo-Tyr-OMe · HCl

H-3,5-Diiodo-Tyr-OMe · HCl is an iodinated tyrosine methyl ester hydrochloride in which the phenolic ring bears two iodine atoms at the 3 and 5 positions, while the α-amino group is present as a protonated salt and the carboxyl functionality is masked as a methyl ester. The stereogenic center of the tyrosine backbone provides defined chiral geometry for downstream peptide coupling and for stereochemically consistent incorporation into peptide or peptidomimetic frameworks. The strongly electron-withdrawing iodine substituents modulate phenolic acidity and aromatic reactivity, enabling controlled derivatization of the tyrosine side chain. The hydrochloride salt form improves handling of the amino ester intermediate and supports compatibility with standard amino acid protection/deprotection and coupling strategies used in peptide building block preparation.

1. Peptide Synthesis

H-3,5-Diiodo-Tyr-OMe · HCl supports peptide building block preparation where the tyrosine α-amino group can be converted into an N-protected amino acid derivative for coupling. The methyl ester provides a protected carboxyl handle that can be activated for amide bond formation under peptide synthesis conditions, while the 3,5-diiodo phenol can be retained or selectively transformed depending on the target sequence and side-chain chemistry. Iodinated aromatic substitution can be leveraged to generate radio-iodinated or detection-compatible peptide analogs after appropriate functional group management. Downstream peptide assembly can proceed through conventional N- and C-terminal strategies, yielding iodinated tyrosine-containing peptides for structure-defined biochemical studies and synthetic methodology development.

2. Chemical Biology Labeling

H-3,5-Diiodo-Tyr-OMe · HCl is suitable for chemical biology workflows that require tyrosine side-chain functionalization for labeling and molecular recognition studies. The 3,5-diiodo phenolic motif can participate in electrophilic aromatic substitution and can be used as a handle for subsequent iodination-state tuning or conjugation-compatible transformations after appropriate protection of the amino and ester functionalities. The amino ester hydrochloride form facilitates controlled conversion into protected intermediates used to incorporate iodinated tyrosine into peptides, linkers, or affinity probes. Resulting labeled biomolecular constructs can serve as analytical and mechanistic tools for studying binding interactions, protease processing, and peptide-mediated recognition events.

3. Peptidomimetics And SAR

H-3,5-Diiodo-Tyr-OMe · HCl enables peptidomimetic construction where the chiral tyrosine backbone and iodinated aromatic ring support structure-activity relationship (SAR) studies. The defined stereochemistry at the α-carbon helps maintain conformational and spatial presentation of the phenolic side chain when incorporated into constrained analogs or substituted scaffolds. The methyl ester can be transformed into amide, acid, or activated derivatives as part of medicinal chemistry-style intermediate preparation, while the iodinated ring can influence lipophilicity, polarizability, and aromatic electronics relevant to binding-site interactions. Synthetic routes can therefore generate a series of iodinated tyrosine-containing analogs for SAR mapping and fragment-to-lead optimization in applied molecular design programs.

4. Analytical Research Standards

H-3,5-Diiodo-Tyr-OMe · HCl is applicable to analytical research as an iodinated tyrosine reference material and derivatization precursor for method development. The methyl ester and amino salt form provide a defined chemical form that can be converted into standardized derivatives for chromatographic or mass spectrometric detection of iodinated tyrosine residues and related metabolites. The 3,5-diiodo substitution pattern yields a distinct spectral signature and can support calibration of assays that monitor iodinated aromatic amino acids in peptide digests or synthetic mixtures. Downstream conversion to acids, amides, or protected intermediates supports consistent sample preparation for analytical workflows in biochemical research and industrial quality control.

5. Pharmaceutical Intermediate Preparation

H-3,5-Diiodo-Tyr-OMe · HCl can serve as a chiral amino acid intermediate for manufacturing-oriented synthesis of iodinated tyrosine derivatives used in pharmaceutical and fine-chemical contexts. The amino ester hydrochloride structure provides a controllable starting point for installing N-protection and converting the ester into coupling-ready forms, enabling incorporation into larger building blocks under scalable peptide-coupling chemistries. The iodinated phenolic ring can be carried through intermediate steps with appropriate protection logic, supporting downstream formation of iodinated aromatic motifs in complex intermediates. Resulting derivatives can be used to assemble iodinated peptide-like fragments, conjugation-ready linkers, or specialized intermediates that require stereochemically defined tyrosine chemistry for applied product development.

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