3-Nitro-L-Phenylalanine contains an L-phenylalanine backbone bearing a nitro substituent at the 3-position of the aromatic ring, classifying it as a naturally derived aromatic amino acid derivative with an electron-withdrawing side-chain functionality. The molecule presents both an amino group and a carboxyl group for zwitterionic behavior in solution, while the side-chain nitro group provides a distinct hydrogen-bonding and redox-active aromatic substituent that can participate in labeling or reactivity studies without changing the core amino acid scaffold. As a free amino acid analogue, it can be used in peptide synthesis and structure-activity or chemical biology experiments where an aromatic nitro handle is required to probe aromatic substitution effects, enable analytical differentiation, or generate nitro-bearing peptide materials.
CAT No: CP16001
CAS No:19883-74-0
Synonyms/Alias:19883-74-0;3-Nitro-L-phenylalanine;(S)-2-amino-3-(3-nitrophenyl)propanoicacid;L-3-NITROPHENYLALANINE;(2S)-2-amino-3-(3-nitrophenyl)propanoicacid;NSC-21948;L-3-Nitrophe;AC1MC5SZ;L-3-NO2-Phe-OH;NCIStruc1_000602;NCIStruc2_000493;SCHEMBL44005;(R)-b-(3-nitrophenyl)alanine;(S)-b-(3-nitrophenyl)alanine;CHEMBL1449772;CTK0I2423;MolPort-001-758-749;NCI21948;ZINC1584113;ANW-73161;CCG-37980;NCGC00013280;AKOS015891099;AM83445;OR14707
3-Nitro-L-Phenylalanine is an L-amino acid bearing a nitro group on the aromatic side chain, making it a structurally distinctive phenylalanine analog used when aromatic electronics and nitro functionality are important to downstream chemistry. In research workflows, the nitro substituent supports electrophile-tolerant handling compared with many more reactive aryl modifications, while also enabling specialized reactivity and labeling strategies that rely on the nitro group's presence. This compound is commonly selected as a non-canonical aromatic building block for peptide and protein-related studies where side-chain substitution pattern matters for analytical readouts or chemical derivatization.
1. Peptide Building Block Use
3-Nitro-L-Phenylalanine is used as an aromatic amino acid building block for peptide synthesis where a nitro-substituted phenyl side chain is required at a defined position. Researchers incorporate this residue into custom peptides for structure-property studies, including investigations of how electron-withdrawing aryl substituents influence peptide conformation, local polarity, and chemical stability under analytical conditions. Solid-phase peptide synthesis workflows frequently employ this type of substituted amino acid to generate peptide standards and analog series for method development, impurity profiling, and comparative characterization of substituted phenylalanine residues.
2. Chemical Biology Derivatization
3-Nitro-L-Phenylalanine is applied in chemical biology and bioconjugation-adjacent workflows that require an aromatic nitro handle for subsequent derivatization or downstream functionalization. Because the nitro group provides a chemically addressable substituent on the side chain, it is often chosen when researchers want to introduce an aryl-functional motif into peptides or small molecules prior to later transformation steps used to generate tagged derivatives, analytical probes, or chemically modified analogs. This makes the compound useful for designing reagent sets where the nitro substitution pattern is the key variable being controlled across analogs.
3. Analytical Standard And LC-MS Workflows
3-Nitro-L-Phenylalanine is widely used as a reference material for analytical method development and quantitative workflows that involve substituted phenylalanine species. In LC-MS and related analytical platforms, the defined nitro-containing aromatic structure supports preparation of calibration or qualification standards for assays monitoring aromatic amino acid analogs, peptide hydrolysates, or derivatized fragments. Analytical teams also use it to support identification and confirmation of nitro-substituted phenylalanine-containing targets in complex mixtures, including peptide synthesis monitoring and characterization of substituted-residue products.
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