3-Nitro-D-tyrosine contains a D-tyrosine backbone bearing a phenolic side chain substituted with a nitro group at the 3-position, making it a proteinogenic amino acid derivative classed as a nitro-substituted aromatic amino acid. The molecule presents a free amino group and a free carboxyl group along with the phenolic hydroxyl and the electron-withdrawing nitro substituent, and its D stereochemistry is specified by the product name. In research settings, this aromatic nitro functionality provides a handle for chemical labeling, conjugation strategies, and structure-activity or enzyme-substrate studies where altered aromatic electronics and polarity relative to tyrosine are relevant, including preparation of modified peptide building blocks after appropriate functional group protection or activation.
CAT No: CP19102
3-Nitro-D-tyrosine is a D-configured tyrosine analog bearing a nitro substituent on the aromatic ring, providing a distinct electron-withdrawing side-chain environment while retaining the phenolic functionality characteristic of tyrosine. This non-proteinogenic amino acid derivative is frequently used in chemical biology and analytical workflows where controlled aromatic substitution and stereochemistry are important for probe behavior, labeling chemistry, or reference measurements. Researchers also value it as a defined building block for preparing modified peptides and for studying how aromatic ring electronics influence binding or reactivity in structure-activity and mechanism-focused studies.
1. Chemical Biology Probes
3-Nitro-D-tyrosine is used as a defined aromatic amino acid building block for constructing chemical biology probes that require a nitro-substituted phenolic side chain. In practice, researchers incorporate it into peptide-based or small-molecule probes to tune aromatic electronics and reactivity at the tyrosine position while maintaining D-stereochemistry to modulate enzymatic recognition and stereochemical outcomes. This makes the reagent relevant for mapping or screening workflows where site-specific incorporation of a tyrosine analog is preferred over using the natural L-form, particularly when the probe's behavior depends on stereochemistry and ring substitution.
2. Modified Peptide Building Block
3-Nitro-D-tyrosine serves as a specialized amino acid building block for preparing modified peptides and peptide fragments in peptide synthesis and SAR studies. Its tyrosine-like phenolic group enables downstream derivatization strategies commonly used for generating labeled or functional peptide variants, while the nitro substitution provides an additional handle for altering aromatic properties that can influence assay readouts. Peptide developers and medicinal chemistry groups use this reagent when they need a non-natural, ring-substituted tyrosine analog at a defined position to compare structure-activity trends or to create peptide standards with distinct mass and chemical signatures.
3. Analytical Reference Compound
3-Nitro-D-tyrosine is widely used as a reference material for analytical method development and targeted quantification workflows that require a stable, well-defined nitro-tyrosine species. Analytical chemists and LC-MS method developers rely on such defined amino acid standards to validate retention behavior, ionization response, and mass spectral features for nitro-substituted aromatic amino acids in complex matrices. Its distinct substitution pattern and D-configuration help differentiate it from endogenous or structurally similar tyrosine forms, supporting more reliable identification and calibration in studies involving modified amino acid detection, derivatized amino acid panels, or comparative analytical experiments.
4. Pharmaceutical Intermediate Development
3-Nitro-D-tyrosine is also used as a defined intermediate in the development of aromatic nitro-substituted tyrosine derivatives for medicinal chemistry and specialty chemical manufacturing. Process and R&D teams incorporate it as a starting material when the target scaffold requires a nitro-substituted phenolic aromatic motif with D-stereochemical control. This supports downstream synthesis of structurally characterized analogs used in lead optimization, structure-activity relationship campaigns, and preparation of defined chemical standards for nonclinical research workflows.
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