Ac-3,5-dinitro-Tyr-OH

Ac-3,5-dinitro-Tyr-OH is a tyrosine-derived amino acid bearing a free carboxylic acid and a 3,5-dinitro-substituted phenolic ring, supplied in an acetylated form (Ac-). The electron-withdrawing dinitro pattern strongly modulates the aromatic phenol's reactivity and makes this scaffold useful where nitro-activated aromatic chemistry, tyrosine analog incorporation, or specialized analytical behavior is required. As a protected/derivatized tyrosine building block rather than a proteinogenic amino acid, it is typically handled as a defined intermediate for peptide-related synthesis and for preparing nitro-phenolic standards and derivatives.

1. Nitro-Tyrosine Building Block

Ac-3,5-dinitro-Tyr-OH is used by peptide chemistry groups to introduce a nitro-activated tyrosine analog into custom peptide sequences or peptide fragments when aromatic electronics and controlled phenolic behavior are important to the target design. Research teams developing tyrosine-modified peptides for structure-property studies, chemical biology probes, or mechanistic mimics often select this scaffold to obtain a consistent 3,5-dinitro-phenyl motif while maintaining a defined amino acid functionality for downstream coupling strategies. The acetylated form helps standardize the N-terminus during intermediate handling and supports reproducible building-block performance across parallel synthesis campaigns.

2. Chemical Biology Probe Intermediates

Ac-3,5-dinitro-Tyr-OH serves as a starting material for constructing nitro-phenolic chemical biology reagents where the 3,5-dinitro substitution is leveraged to tune aromatic reactivity and labeling chemistry. Chemical biology laboratories and probe-development teams commonly use nitro-tyrosine motifs to create defined aromatic handles for subsequent derivatization steps, including attachment to linkers, conversion into further functionalized derivatives, or incorporation into peptide-based probes. This product's tyrosine backbone provides a familiar stereochemical framework for integrating into peptide-like constructs, while the dinitro phenyl ring supports specialized downstream transformations used in probe workflows.

3. Analytical Standards And Derivatives

Ac-3,5-dinitro-Tyr-OH is used to prepare analytical references and derivative standards for LC-MS and related analytical workflows targeting nitro-phenolic aromatic species. Analytical chemistry groups often require well-defined nitro-tyrosine analogs to validate retention behavior, fragmentation patterns, and method performance when studying nitro-phenol-containing metabolites, reaction products, or derivatization outcomes. Because the scaffold is structurally specific (3,5-dinitro substitution with a tyrosine-derived phenolic core), it is well suited for generating standards and calibration components that support accurate identification and characterization of related nitro-phenolic compounds in complex mixtures.

4. Pharmaceutical Intermediate Development

Ac-3,5-dinitro-Tyr-OH is also applied as a pharmaceutical-intermediate building block in medicinal chemistry and process development settings where a nitro-phenolic tyrosine-like motif is required for SAR (structure-activity relationship) exploration or for preparing downstream aryl-functionalized intermediates. Development chemists use this compound to access a defined aromatic substitution pattern and a tyrosine-derived carbon framework that can be elaborated into more complex structures for screening libraries or late-stage intermediate routes. The presence of a free carboxylic acid and the acetylated amino functionality make it a practical scaffold for controlled conversion into subsequent coupling-ready or derivatization-ready intermediates within industrial and custom synthesis workflows.

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