3-Nitro-D-Phenylalanine is a non-proteinogenic, aromatic amino acid derivative featuring a D-configuration at the α-carbon and a phenyl side chain bearing a meta-position nitro substituent. The molecule contains a free α-amino group and a free carboxyl group alongside the electron-withdrawing nitro functionality on the aromatic ring, which can influence polarity and hydrogen-bonding behavior relative to unsubstituted phenylalanine. In chemical biology and peptide chemistry workflows, it is used as a substrate-like building block for incorporating a nitro-bearing aromatic residue into synthetic peptides or for structure-activity and labeling studies where the nitro group provides a distinct chemical handle for downstream derivatization and analytical differentiation.
CAT No: CP16002
CAS No:169530-97-6
Synonyms/Alias:169530-97-6;(R)-2-Amino-3-(3-nitrophenyl)propanoicacid;3-Nitro-D-phenylalanine;D-3-NITROPHENYLALANINE;(2R)-2-amino-3-(3-nitrophenyl)propanoicacid;D-3-Nitrophe;AC1OCT0Y;D-3-NO2-Phe-OH;SCHEMBL8083539;SCHEMBL13660573;CTK8B7889;MolPort-001-758-750;ZINC2046240;ANW-58868;AM83446;OR14708;AJ-33408;AK-60092;KB-32989;TR-007413;FT-0697810;ST24035309;Y6714;K-5242
3-Nitro-D-Phenylalanine is a D-configured, non-proteinogenic phenylalanine analogue bearing a nitro group on the aromatic ring, providing an electronically distinct side chain for structure-property studies and chemical biology workflows. Its aromatic nitro functionality makes it a useful building block for preparing peptidomimetics and aromatic side-chain variants where altered electronics and reactivity are required. Researchers also use this compound as a defined chiral amino acid derivative for synthetic route development and analytical method support when a D-phenylalanine stereochemical motif is needed.
1. Peptidomimetic Building Block
3-Nitro-D-Phenylalanine is used by medicinal chemistry and peptide chemistry groups to construct peptidomimetics and modified peptide segments that incorporate a D-phenylalanine stereocenter while introducing a nitro-substituted aromatic side chain. This enables systematic structure-activity or structure-property exploration in custom peptide and peptidomimetic libraries, where aromatic electronics and side-chain substitution patterns are tuned without changing the backbone stereochemical framework. The compound is particularly relevant for preparing defined analogs for downstream biological evaluation workflows run by peptide discovery teams, as well as for generating well-characterized standards for characterization of modified peptide scaffolds.
2. Chemical Biology Probes
3-Nitro-D-Phenylalanine is employed in chemical biology research as an aromatic nitro-containing amino acid handle for probe and labeling strategy development. Teams designing side-chain-modified peptides or small-molecule conjugates often select nitro-substituted aromatic amino acid building blocks to introduce a distinct functional signature that can be tracked analytically and incorporated into target-binding or assay-compatible constructs. In practice, it supports the synthesis of defined probe precursors used for studying molecular recognition, mapping structure effects in binding scaffolds, and generating reproducible reagents for assay development where stereochemical control (D-configuration) and aromatic substitution are important for interpretability.
3. Pharmaceutical Intermediate Development
3-Nitro-D-Phenylalanine is used as a chiral amino acid intermediate in pharmaceutical intermediate development and specialty chemical manufacturing, especially when a D-phenylalanine-derived motif with a nitro-substituted aromatic ring is required for late-stage diversification. Process and synthesis development groups value this building block for preparing substituted aromatic amino acid derivatives that can feed into subsequent functionalization steps toward more complex intermediates. Because the nitro group provides a chemically informative aromatic substituent, it is commonly leveraged in development pipelines that require robust, well-defined starting materials for downstream transformation and analytical traceability.
4. Analytical Reference Material
3-Nitro-D-Phenylalanine serves as a defined analytical reference and characterization standard for laboratories working with nitro-substituted amino acid derivatives, including method development for LC-MS and related workflows. Analytical chemists and quality control teams use stereochemically defined D-amino acid standards to confirm identity, monitor derivatization or conversion steps, and support calibration or qualification of analytical signals for aromatic nitro-containing species. The compound's fixed structure and stereochemistry make it a practical choice when researchers need an unambiguous comparator for studying modified peptide fragments, amino acid building block integrity, or intermediate purity in research and development settings.
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