(S)-α-Methyl-2-nitrophenylalanine·H2O contains an α-methylated amino acid backbone bearing a benzyl side chain substituted with a nitro group, and it is present as a hydrated salt form (·H2O). The molecule features both an amino functional group and a carboxyl functional group, with the (S) stereochemical configuration indicated at the α-carbon and the nitro substituent providing a strongly electron-withdrawing aromatic functionality that can influence side-chain polarity and reactivity. In peptide and chemical biology research, this non-proteinogenic, aromatic nitro-bearing amino acid is used as a defined building block for incorporating sterically modified residues into peptide analogues and for structure-activity studies or analytical labeling strategies that rely on the nitro-functional handle.
(S)-α-Methyl-2-nitrophenylalanine·H2O is a chiral, α-methylated amino acid bearing a 2-nitrophenyl side chain, supplied as a hydrate salt form. The combination of the α-methyl stereocenter and the ortho-nitro aromatic functionality makes it a useful stereodefined building block for preparing sterically constrained amino acid derivatives and nitroaryl-containing peptide analogs. In research workflows, the nitro group also provides a convenient handle for downstream derivatization and analytical characterization of aromatic amino acid motifs.
1. Peptidomimetic Building Blocks
(S)-α-Methyl-2-nitrophenylalanine·H2O is used as a stereodefined amino acid building block in peptidomimetic and modified peptide synthesis, where α-methyl substitution is leveraged to influence conformation and local backbone geometry in peptide analogs. Medicinal chemistry groups and peptide-chemistry teams incorporate this residue into solution-phase or solid-phase peptide assembly to generate nitroaryl-containing analogs for structure-activity relationship studies and stability-focused analog libraries. The hydrate form supports consistent weighing and handling for downstream coupling into protected amino acid strategies, while the 2-nitrophenyl side chain provides an aromatic reporter motif that can be monitored during purification and characterization.
2. Structure-Activity SAR Probes
(S)-α-Methyl-2-nitrophenylalanine·H2O is commonly selected by small-molecule and peptide lead-optimization teams as a residue-level probe for mapping how steric bulk at the α-position and an ortho-nitroaryl side chain affect physicochemical properties and structure-function trends. Researchers use it to generate focused series of analogs in which the nitroaryl group serves as a distinct chemical signature, enabling comparative LC-MS tracking and chromatographic discrimination between closely related variants. This makes the compound particularly useful when building SAR panels that require a well-defined, chiral aromatic amino acid motif rather than a generic phenylalanine-like substitution.
3. Analytical Derivatization Standards
(S)-α-Methyl-2-nitrophenylalanine·H2O is applied in analytical method development and reference material preparation for workflows that monitor nitroaryl amino acid fragments, peptide hydrolysates, or labeled/derivatized aromatic amino acid species by LC-MS. Analytical chemistry laboratories use the defined stereochemistry and characteristic nitroaromatic functionality to support method specificity when distinguishing α-methylated aromatic amino acid residues from structurally similar standards. The hydrate form is often convenient for preparing reproducible calibration or check solutions for instrument qualification and for verifying retention-time and mass-to-charge behavior of nitroaryl-containing analytes.
4. Pharmaceutical Intermediate Synthesis
(S)-α-Methyl-2-nitrophenylalanine·H2O is also used as a chiral intermediate in pharmaceutical intermediate development where an α-methylated amino acid framework and an ortho-nitrophenyl functionality are required as key synthetic elements. Chemical development teams incorporate it into downstream sequences to access nitroaryl-containing amino acid derivatives, which can then be further transformed into protected or functionalized intermediates for medicinal chemistry programs. The stereodefined starting material supports consistent generation of chiral downstream building blocks, and the nitro group provides a chemically distinct aromatic handle for subsequent functional group interconversions during process development.
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