3,5-Dinitro-D-tyrosine is a non-proteinogenic, D-configured tyrosine derivative featuring a phenolic aromatic ring substituted with two nitro groups at the 3 and 5 positions and a side chain consistent with the tyrosine scaffold. The molecule contains a free amino group and a free carboxyl group, and its nitro-substituted phenol provides a strongly electron-withdrawing aromatic functionality that can participate in redox-active and electrophilic aromatic substitution chemistry while remaining compatible with standard amino-acid handling in synthetic workflows. In research contexts, it is used as a chemically defined amino acid building block for peptide and conjugate synthesis and as an aromatic nitro-functional handle for structure-activity studies, chemical labeling strategies, and analytical method development involving nitrotyrosine-like motifs.
CAT No: CP18402
3,5-Dinitro-D-tyrosine is a D-configured tyrosine derivative bearing two nitro substituents at the 3- and 5-positions on the aromatic ring, creating a strongly electron-deficient phenolic side chain. This substitution pattern is widely used to introduce a defined, highly characteristic aromatic motif for chemical biology workflows and analytical applications where nitrotyrosine-like chemistry and spectroscopic detectability are valuable. The compound's rigid aromatic functionality and phenolic group make it a practical building block for generating defined nitroarene-containing peptide or protein standards and for studying nitroaromatic modifications in controlled systems.
1. Nitroaromatic Peptide Building Block
3,5-Dinitro-D-tyrosine is used as a specialty amino acid building block for peptide synthesis workflows that require an explicitly defined dinitrotyrosine residue. Researchers incorporate this residue into short peptides and peptide mimics to model nitroaromatic modifications with precise stereochemical definition, enabling controlled structure-property studies and method development for downstream detection. In peptide-based assays and chemical biology experiments, the dinitro-substituted aromatic ring provides a strong chemical handle for differentiating and tracking the modified site during sample preparation and analysis.
2. Analytical Standards For LC-MS
3,5-Dinitro-D-tyrosine is frequently selected as a reference material for analytical method development and quantitative workflows targeting nitroaromatic amino acid derivatives. Its well-defined substitution pattern supports reproducible calibration and retention behavior in LC-MS-based assays used to monitor modified tyrosine species in complex matrices. Analytical chemists and proteomics method developers also use it to verify derivatization and extraction performance when preparing standards for targeted mass spectrometry panels focused on nitroarene-containing residues.
3. Chemical Biology Modification Probes
3,5-Dinitro-D-tyrosine is applied in chemical biology studies that require a defined nitroaromatic motif to probe modification chemistry and site-specific labeling strategies in controlled experimental systems. Scientists use it to construct defined modified peptide or protein fragments that can be used to evaluate how nitroaromatic residues behave during binding, enrichment, or analytical readouts. The electron-deficient dinitroarene character helps create a distinct chemical identity compared with unmodified tyrosine, supporting clearer interpretation in experiments designed to distinguish modified from unmodified aromatic residues.
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