3-(2-Naphthyl)-D-Alanine is a non-proteinogenic, aromatic amino acid derivative featuring a D-configured α-amino acid backbone bearing a 2-naphthyl substituent on the side chain. The molecule contains a free amino group and a carboxyl group, with the bulky polycyclic aromatic side chain providing hydrophobic and π-stacking functionality that can influence conformational preferences and binding interactions in peptide or small-molecule contexts. In synthesis and chemical biology workflows, it is used as a building block for incorporating a naphthyl-bearing residue into peptides and peptidomimetics for structure-activity studies, fluorescence or spectroscopic labeling strategies when paired with appropriate detection methods, and analytical method development where aromatic side-chain contrast is required.
CAT No: CP22207
3-(2-Naphthyl)-D-Alanine is a D-configured, non-proteinogenic amino acid bearing a bulky 2-naphthyl side chain that provides strong hydrophobic character and aromatic surface for structure-activity and binding studies. Its stereochemical definition and aromatic functionality make it a useful building block for incorporating a constrained, non-natural residue into peptides and peptidomimetics where side-chain identity is a key design variable. Researchers also use this scaffold as a defined chiral amino acid intermediate to prepare analytical reference materials and structure-defined conjugates for chemical biology workflows.
1. Peptidomimetic Building Blocks
3-(2-Naphthyl)-D-Alanine is used by medicinal chemistry and chemical biology teams to introduce a 2-naphthyl aromatic residue into peptides, peptidomimetics, and structured oligomers where hydrophobic/aromatic side-chain effects are being tuned. The D-stereochemistry supports incorporation into stereochemically defined sequences for SAR studies, allowing downstream comparison of analogs that differ specifically at the non-natural side chain. This amino acid is commonly selected when a strong aromatic moiety is required to probe binding-site interactions, stabilize defined conformations in solution, or generate sequence-defined materials for receptor/ligand interaction experiments.
2. Chiral SAR And Analogue Libraries
3-(2-Naphthyl)-D-Alanine supports structure-activity relationship (SAR) library synthesis by providing a consistent, chiral aromatic handle that can be varied at the residue level without changing the peptide backbone architecture. In practice, researchers use it to generate matched analog series for studying how aromatic size, hydrophobicity, and steric profile influence activity readouts in binding and functional assays. The rigid naphthyl group also helps teams interpret structure-property relationships when comparing analogs that use different aromatic substitutions, enabling more direct attribution of observed differences to the side-chain identity.
3. Chemical Biology Binding Probes
3-(2-Naphthyl)-D-Alanine is applied in chemical biology projects that require a defined aromatic amino acid motif to support binding-probe construction and interaction mapping. The 2-naphthyl side chain can serve as a recognizable hydrophobic/aromatic element within a larger probe scaffold, supporting workflows where researchers evaluate ligand-target association using structurally matched compounds. This product is especially useful for teams building probe analogs that must retain stereochemical control while embedding a strong aromatic reporter group into peptide-like structures for downstream characterization and comparative binding studies.
4. Analytical Reference Standards
3-(2-Naphthyl)-D-Alanine is used to prepare chemically defined reference materials for analytical method development and characterization of peptide or peptidomimetic intermediates and final compounds. Laboratories use the stereochemically defined, aromatic amino acid to confirm identity in synthesis workflows, support method validation for LC-based assays, and enable consistent comparison across batches of structure-defined analogs. Its non-natural nature and defined side-chain structure make it a practical standard component when tracking incorporation of a specific aromatic residue in complex mixtures.
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