3-(1-Naphthyl)-D-Alanin is a non-proteinogenic, aromatic amino acid derivative featuring a D-alanine backbone substituted at the 3-position with a 1-naphthyl group, yielding a bulky, hydrophobic side chain distinct from standard aliphatic residues. The molecule contains a free amino group and a carboxyl group characteristic of amino acid scaffolds, with stereochemistry indicated as the D configuration at the α-carbon and an aryl substituent that can participate in π-π interactions and hydrophobic contacts. As a structurally modified amino acid, it is used as a substrate building block in peptide and peptidomimetic synthesis and in chemical biology studies where aromatic side-chain placement, fluorescence/UV-active labeling potential, or structure-activity comparisons require a naphthyl-bearing residue.
CAT No: CP22201
3-(1-Naphthyl)-D-Alanin is a D-configured alanine derivative bearing a 1-naphthyl substituent at the 3-position, creating a hydrophobic, aromatic side-chain analogue that is commonly used as a non-natural amino acid building block in peptide and peptidomimetic research. Its rigid naphthalene motif supports hydrophobic and π-interaction-driven structure-property studies, while the stereodefined alanine core provides a controlled chiral handle for sequence-defined synthesis. Researchers also use this compound as a specialized intermediate when preparing aromatic amino acid analogs for chemical biology and medicinal chemistry workflows.
1. Peptidomimetic Building Block
3-(1-Naphthyl)-D-Alanin is used by medicinal chemistry and peptide chemistry groups to introduce a D-alanine stereocenter combined with a naphthyl aromatic side chain into peptides, peptidomimetics, and sequence-defined analogs. The 1-naphthyl group is particularly valuable for mapping how increased hydrophobic surface area and aromatic stacking contributions influence conformation, binding-site engagement, and structure-activity relationships in synthetic ligand series. Because the compound is stereodefined, it supports consistent analog-to-analog comparisons where stereochemistry at the amino acid center is a key variable.
2. Structure-Activity SAR Probes
3-(1-Naphthyl)-D-Alanin is frequently selected for SAR probe synthesis in projects that require non-natural amino acid substitutions to interrogate the role of aromatic functionality and hydrophobic character. Chemical biology teams incorporate this aromatic alanine analogue into constrained or semi-flexible peptide scaffolds to generate focused libraries that vary side-chain size and π-interaction capability without changing the alanine backbone stereochemical identity. This makes the compound useful for downstream hit-to-lead optimization studies where researchers need interpretable structure changes tied to a well-defined aromatic motif rather than a generic hydrophobic substituent.
3. Chiral Intermediate For Analog Synthesis
3-(1-Naphthyl)-D-Alanin serves as a chiral amino acid intermediate for the preparation of further aromatic alanine derivatives used across research-grade synthesis campaigns. Process and R&D chemists employ it to build series of analogs where the naphthyl-bearing alanine scaffold is retained while additional functional group modifications are introduced for downstream coupling, tagging, or formulation-relevant property tuning. Its D-configuration supports stereochemically consistent intermediate supply for iterative medicinal chemistry and materials-facing development pipelines that rely on reliable chiral building blocks.
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