2-Nitro-DL-tryptophan is a substituted tryptophan amino acid derivative in which the indole ring bears a nitro group at the 2-position, and it is supplied as a DL mixture, indicating both stereoisomeric forms at the alpha carbon. The molecule contains the standard amino and carboxyl functional groups of an amino acid, while the electron-withdrawing nitro substituent on the indole side chain modulates aromatic reactivity and provides a handle for chemical derivatization or spectroscopic/analytical differentiation relative to unsubstituted tryptophan. As a non-proteinogenic, structurally modified amino acid, it is used in peptide and chemical biology workflows where aromatic side-chain substitution, side-chain electronics, or isotopic/chemical tagging strategies require an indole-bearing nitro functionality for synthesis of more complex amino acid and peptide derivatives.
CAT No: CP25003
2-Nitro-DL-tryptophan is a nitro-substituted tryptophan analog available as a DL mixture, combining the indole aromatic scaffold with an electron-withdrawing nitro group at the 2-position. This amino acid derivative is used as a chemically defined tryptophan variant for studies that require an altered indole environment, including spectroscopic and reactivity-focused labeling strategies. Its zwitterionic amino acid functionality supports incorporation into peptide-like constructs and analytical workflows where tryptophan position-specific behavior is compared under controlled conditions.
1. Peptide Analog Building Block
2-Nitro-DL-tryptophan is used by peptide chemistry groups to prepare tryptophan-containing peptide analogs and modified peptide segments where the indole electronics are intentionally perturbed by the 2-nitro substituent. Researchers commonly select this building block when they need a defined aromatic residue to probe how changes to the indole ring influence peptide conformation, local packing, or chemical stability during downstream handling and characterization. Because it is supplied as a DL mixture, it is often chosen for comparative studies that focus on chemical reactivity or analytical signatures rather than stereochemically pure residue behavior.
2. Chemical Biology Labeling Studies
2-Nitro-DL-tryptophan supports chemical biology workflows that investigate tryptophan-like aromatic interactions and nitro-activated reactivity in protein or peptide contexts. Chemical biology and biomolecular engineering teams use this residue to introduce a tryptophan mimic into peptide probes for mapping aromatic microenvironments, monitoring residue-specific chemical changes, or generating defined standards for interpreting mass spectrometry and chromatographic readouts. The nitro group provides a distinct chemical handle compared with unmodified tryptophan, enabling controlled experiments where the indole environment must be differentiated without relying on heterogeneous mixtures of native residues.
3. Analytical Standards For Tryptophan Analogues
2-Nitro-DL-tryptophan is widely used as an analytical reference material for LC-MS and related quantification workflows involving tryptophan analogs and nitroindole-containing peptides. Analytical chemistry laboratories employ it to build calibration strategies, verify retention-time behavior, and support method development when distinguishing nitro-substituted indole species from native tryptophan-containing components. The defined amino acid form also helps standardize sample preparation and interpretation in studies where aromatic residue modifications are expected to shift ionization and fragmentation patterns relative to conventional tryptophan.
4. Pharmaceutical Intermediate Development
2-Nitro-DL-tryptophan is utilized in pharmaceutical intermediate development and specialty chemical manufacturing as a structurally defined tryptophan derivative for constructing nitroindole-containing intermediates. Process and R&D chemists often choose this starting material when the indole scaffold with a nitro substituent is required as a building block for downstream synthesis of aromatic heterocycle derivatives, protected amino acid intermediates, or customized aromatic fragments used in medicinal chemistry programs. The presence of both the amino acid functionality and the nitro-substituted indole core makes it a practical feedstock for assembling chemically consistent intermediates for further derivatization and analytical verification.
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