3-(2-Naphthyl)-L-Alanine is an L-configured, proteinogenic amino acid analogue in which the side chain bears a 2-naphthyl aromatic group, replacing the native side-chain functionality while retaining the α-amino acid backbone with both an amino and a carboxyl group. The molecule contains a primary amino group and a carboxylic acid that can exist as zwitterionic forms under appropriate conditions, and its bulky, hydrophobic naphthalene ring provides a rigid aromatic handle for π-π and hydrophobic interactions in assembled peptide structures. As a non-natural amino acid suitable for peptide synthesis and structure-activity studies, it can be incorporated into peptides to introduce an aromatic chromophore for chemical biology labeling, binding studies, or analytical methods that benefit from naphthalene-containing side chains.
CAT No: CP22208
CAS No:58438-03-2
Synonyms/Alias:2,6-Diaminopimelicacid;2,6-Diaminoheptanedioicacid;583-93-7;dl-2,6-Diaminoheptanedioicacid;DIAMINOPIMELICACID;1,5-DiaminoheptanedioicAcid;D1377_SIGMA;Heptanedioicacid,2,6-diamino-;DL-alpha,epsilon-Diaminopimelicacid;(2R,6R)-2,6-diaminoheptanedioicacid;ST049753;ll-diaminopimelate;meso-diaminopimelate;D,L-diaminopimelate;LL-A2pm;D,L-meso-diaminoheptanedioate;(6R,2s)-diaminopimelicacid;meso-2,6-diaminoheptanedioate;M-DAP;L,L-A2pm;C7H14N2O4;D,L-DAP;L,L-DAP;meso-1-alpha,epsilon-diaminopimelate;bmse000401
3-(2-Naphthyl)-L-Alanine is an L-amino acid bearing a 2-naphthyl substituent at the beta position, providing a rigid, hydrophobic aromatic side chain well suited for structure-activity relationship studies and aromatic recognition design. As an unprotected amino acid building block, it is commonly handled as a peptide-compatible intermediate for creating aromatic-rich peptide analogs and for introducing a defined naphthyl moiety into larger synthetic sequences. Its stereodefined backbone supports consistent incorporation into peptide frameworks and downstream analytical characterization where the aromatic side chain is the primary functional element.
1. Aromatic Peptide Building Block
3-(2-Naphthyl)-L-Alanine is used as a specialized amino acid building block for peptide synthesis where a naphthyl-containing residue is required to tune hydrophobicity, aromatic stacking, and local steric environment. Research groups developing peptide libraries for receptor-binding studies, enzyme substrate analogs, or conformation-sensitive peptide probes often select this residue to introduce a bulky polyaromatic side chain that can strongly influence folding and intermolecular interactions. Because the product is provided as an L-amino acid, it supports stereochemically consistent sequence design in custom peptide synthesis workflows, including both small-molecule peptide analogs and longer peptide constructs used for binding and stability comparisons.
2. Medicinal Chemistry SAR Intermediate
3-(2-Naphthyl)-L-Alanine serves as a practical intermediate for medicinal chemistry programs that require incorporation of a defined naphthyl-bearing amino acid motif into peptidomimetic scaffolds. Medicinal chemistry and chemical biology teams use this building block to generate analog series where aromatic substitution patterns are systematically varied, enabling structure-activity relationship evaluation driven by changes in lipophilicity and aromatic surface area. The beta-(2-naphthyl) side chain provides a chemically stable, nonpolar handle that can be carried through to downstream coupling, derivatization, and final scaffold assembly, supporting reproducible SAR synthesis for lead optimization studies and mechanistic analog generation.
3. Chemical Biology Binding Probes
3-(2-Naphthyl)-L-Alanine is frequently employed in chemical biology workflows to construct aromatic-rich peptide or peptidomimetic probes that report on binding interactions through the presence of a naphthyl group. Researchers investigating hydrophobic pocket recognition, aromatic stacking contributions, or ligand-protein interaction trends use this residue to create probe analogs where the naphthyl moiety is the key interaction element. In these applications, the defined L-configuration and the rigid polyaromatic side chain help maintain consistent probe geometry across analog series, supporting comparative binding studies using standard biochemical and biophysical assays.
4. Analytical Reference Standards
3-(2-Naphthyl)-L-Alanine is also used as a defined chemical reference for analytical method development and characterization of aromatic-containing peptide or peptidomimetic samples. Analytical chemistry teams rely on such well-characterized amino acid building blocks to support LC-MS identification, retention-time benchmarking, and calibration strategies when naphthyl-containing fragments or residues are expected. The presence of a single, distinctive 2-naphthyl aromatic side chain makes it a useful anchor compound for verifying fragment assignments and for preparing consistent standards used in method validation workflows for complex peptide mixtures.
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