Ac-3,5-dinitro-Tyr-OEt contains a Tyr-derived aromatic amino acid framework bearing two nitro substituents at the 3- and 5-positions on the phenyl ring, with the amino group acetylated (Ac-) and the carboxyl group converted to an ethyl ester (OEt), making it an amino acid derivative rather than a free amino acid. The molecule therefore presents an acetyl-protected amino functionality and an esterified carboxyl group while retaining the phenolic side-chain of tyrosine, whose electron-withdrawing nitro substituents modulate aromatic reactivity and can support labeling or derivatization chemistry. Ac-3,5-dinitro-Tyr-OEt is used in peptide and amino-acid chemistry workflows as a protected, esterified tyrosine building block for preparing nitro-substituted peptide analogues and for analytical or chemical-biology studies that require a defined, nitro-functional aromatic residue.
CAT No: CP26969
CAS No:29358-99-4
Synonyms/Alias:Ac-3,5-dinitro-Tyr-OEt;29358-99-4;N-Acetyl-3,5-dinitro-L-tyrosineethylester;SCHEMBL7638610;Jsp005589;CTK8F7527;ZINC2571400;CA-509;Acetyl-3,5-dinitro-L-tyrosineethylester;FT-0629793;FT-0638849
Ac-3,5-dinitro-Tyr-OEt is an O-ethyl ester derivative of a tyrosine scaffold bearing two nitro substituents at the 3- and 5-positions on the aromatic ring, with the N-terminus acetylated to reduce competing reactivity during downstream handling. This highly electron-withdrawing dinitro-phenyl motif makes the compound a practical aromatic-tagged amino acid intermediate for preparing nitro-substituted tyrosine derivatives and for building blocks used in analytical and chemical-biology workflows where defined aromatic substitution patterns are required.
1. Nitro-Tyrosine Intermediate Synthesis
Ac-3,5-dinitro-Tyr-OEt is used by synthetic chemists and peptide-material developers as a protected, pre-functionalized tyrosine-derived intermediate for constructing 3,5-dinitro-tyrosine analogs. The acetylated amino terminus and ethyl ester format support controlled reactivity in multi-step sequences, enabling late-stage introduction of the dinitro aromatic pattern into larger fragments such as substituted phenolic amino acid derivatives, conjugatable tyrosine analogs, or specialty building blocks for structure-activity relationship studies in aromatic substitution chemistry.
2. Aromatic Labeling Building Block
Ac-3,5-dinitro-Tyr-OEt is commonly selected when a defined, strongly substituted nitro-tyrosine aromatic motif is needed as a chemical label or reference fragment in labeling and derivatization workflows. Researchers in chemical biology and analytical chemistry use this type of nitro-substituted tyrosine derivative to generate standards and defined analogs that maintain a consistent aromatic substitution pattern, supporting reproducible downstream derivatization, chromatographic behavior control, and method development for assays that rely on the presence of the 3,5-dinitro-phenyl signature.
3. Peptide Fragment Derivatization
Ac-3,5-dinitro-Tyr-OEt is applied in custom peptide and peptidomimetic development as a tyrosine-derived fragment precursor for incorporating a 3,5-dinitro-substituted aromatic residue into larger constructs. In workflows where a specific tyrosine substitution pattern must be introduced without disturbing other functional groups, the acetylated amino functionality and esterified carboxyl group provide a stable intermediate form for assembling substituted aromatic residues into peptide-like scaffolds used for binding studies, protease substrate analog generation, or materials-oriented polymer/peptide hybrid synthesis.
4. Analytical Standard Preparation
Ac-3,5-dinitro-Tyr-OEt is used by analytical method developers to prepare defined nitro-tyrosine standards and calibration/qualification materials for LC-based characterization of aromatic-substituted tyrosine derivatives. The fixed substitution pattern and controlled functional group state (acetylated amino, ethyl ester) help ensure that the reference material matches the chemical identity of target derivatives used in derivatization-based assays, impurity profiling, and impurity-to-structure confirmation during pharmaceutical intermediate development and specialty chemical quality control.
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