3-Nitro-DL-Phenylalanine

3-Nitro-DL-Phenylalanine is a nitro-substituted phenylalanine derivative supplied as a DL mixture, providing both D- and L- stereoisomers for research workflows that require racemic access to the aromatic side chain. The nitro group on the benzyl ring introduces a strongly electron-withdrawing functionality that is commonly leveraged for chemical reactivity and for spectroscopic or analytical differentiation versus unsubstituted phenylalanine. As an amino acid building block, it is frequently used in peptide and peptidomimetic synthesis, as well as in labeling and analytical standard preparation where the nitro substituent provides a distinct mass and chemical handle.

1. Peptidomimetic Building Block

3-Nitro-DL-Phenylalanine is used as an amino acid building block for preparing modified peptides and peptidomimetics in medicinal chemistry and chemical biology programs that explore the impact of aromatic ring electronics and substituent effects. Researchers incorporate this nitro-phenylalanine unit into short peptide scaffolds, SAR libraries, and constrained analogs to probe how electron-withdrawing substitution influences conformation, physicochemical behavior, and downstream chemical stability under assay conditions. The DL stereochemical format supports screening approaches where access to both stereoisomers is required to evaluate stereochemical effects without committing to a single enantiomer at early stage development.

2. Chemical Biology Labeling Studies

3-Nitro-DL-Phenylalanine is applied in chemical biology workflows that require a nitro-functionalized aromatic amino acid to introduce a chemically distinctive handle into peptide-based probes or conjugates. In practice, this enables researchers to generate probe libraries where the nitro substituent provides a differentiating tag for subsequent detection, purification tracking, or orthogonal downstream derivatization steps during probe construction. Teams working on mechanistic studies and interaction mapping often select nitro-substituted amino acid building blocks to create structurally defined reagents that can be distinguished from phenylalanine-containing controls in analytical readouts.

3. Analytical Standards And LC-MS Workflows

3-Nitro-DL-Phenylalanine is frequently used to prepare analytical reference materials and calibration components for LC-MS and related quantification workflows where a nitro-substituted phenylalanine provides a clear, non-overlapping signal relative to common amino acid backgrounds. Analytical method developers and metabolomics or proteomics researchers use this compound as a structurally matched standard to support identification confidence, retention-time anchoring, and mass-based confirmation in experiments involving nitro-aromatic amino acid variants. The DL composition is particularly useful when the analytical goal is to quantify total nitro-phenylalanine content irrespective of enantiomeric distribution, or when sample preparation and measurement pipelines are designed to treat stereoisomers collectively.

1. Oleic acid and glucose regulate glucagon-like peptide 1 receptor expression in a rat pancreatic ductal cell line

2. Myotropic activity of allatostatins in tenebrionid beetles

3. Uncarboxylated osteocalcin decreases insulin-stimulated glucose uptake without affecting insulin signaling and regulators of mitochondrial biogenesis in myotubes

4. GLP-1, exendin-4 and C-peptide regulate pancreatic islet microcirculation, insulin secretion and glucose tolerance in rats

5. Myotropic activity and immunolocalization of selected neuropeptides of the burying beetle Nicrophorus vespilloides (Coleoptera: Silphidae)