3-Nitro-DL-tyrosine contains an aromatic phenol-bearing amino acid framework in which a nitro substituent is located at the 3-position of the phenyl ring, classifying it as a tyrosine derivative with an electron-withdrawing side chain. The molecule bears both an α-amino group and a carboxyl group, and the "DL" designation indicates a racemic mixture of stereoisomers at the α-carbon, while the phenolic hydroxyl provides a polar, hydrogen-bonding functionality and the nitro group offers additional redox and electrophilic character typical of nitroaromatics. As a substituted aromatic amino acid, it is used as a building block for peptide and peptidomimetic synthesis to introduce a defined nitro-phenyl side chain for structure-activity studies, chemical biology labeling strategies, or analytical method development involving nitroaromatic residues.
CAT No: CP19103
3-Nitro-DL-tyrosine is a nitro-substituted tyrosine analog supplied as a DL mixture, featuring the phenolic side chain characteristic of tyrosine alongside a meta-nitro group that strongly influences aromatic electronics and reactivity. As an amino acid building block, it is commonly used in peptide and small-molecule synthesis where the nitro-phenyl motif serves as a chemical handle for subsequent derivatization or as an aromatic functionality for probing structure-property relationships. Its free amino acid form also makes it a practical intermediate for preparing labeled or functionalized aromatic derivatives used in chemical biology and analytical workflows.
1. Peptide Building Block Use
3-Nitro-DL-tyrosine is used as an aromatic amino acid building block for preparing peptides and peptidomimetic fragments that incorporate a nitro-phenyltyrosine motif. Researchers in peptide chemistry and custom peptide manufacturing select this building block when they need a tyrosine-like phenolic side chain while introducing an electron-withdrawing nitro substituent to modulate local electronics and enable downstream functionalization of the aromatic ring. The DL stereochemical mixture is particularly relevant for workflows focused on chemical incorporation into synthetic peptides rather than stereodefined proteinogenic studies.
2. Aromatic Derivatization Intermediate
3-Nitro-DL-tyrosine is widely applied as a pharmaceutical-intermediate style substrate for converting the nitro aromatic functionality into downstream derivatives used in medicinal chemistry and specialty chemical synthesis. Synthetic teams use it to access nitro-to-amino or other nitro-functional transformation pathways that generate new aromatic substitution patterns while retaining the amino acid backbone for further coupling, esterification, or amide formation. This makes the material useful for building libraries of aromatic analogs and for preparing tyrosine-derived scaffolds where the nitro group provides a controllable chemical entry point.
3. Chemical Biology Probe Synthesis
3-Nitro-DL-tyrosine is employed in chemical biology research to construct aromatic probes and labeled fragments that exploit the distinct reactivity and electronic character of the nitro-substituted phenyl ring. Chemical biology groups incorporate this building block into probe precursors to generate tyrosine-based aromatic motifs that can be further transformed into detection-ready or affinity-ready derivatives, including conjugatable aromatic intermediates. The presence of the amino acid functionality supports straightforward attachment to linkers or coupling partners used in probe assembly pipelines.
4. Analytical Reference Derivative Prep
3-Nitro-DL-tyrosine is used for preparing analytical standards and calibration materials for method development in LC-MS and related workflows targeting nitro-aryl amino acid motifs. Analytical chemistry teams choose this compound as a starting material for generating reference derivatives that match expected analyte classes, improving identification confidence when monitoring nitro-substituted aromatic species in complex mixtures. Its defined nitro/phenolic substitution pattern makes it a practical precursor for standard preparation when the analytical target is tied to this specific aromatic substitution motif.
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