3-(1-Naphthyl)-L-Alanine is an L-alanine derivative bearing a 1-naphthyl substituent on the side chain, placing it within the class of aromatic, non-proteinogenic amino acids used for structure-function studies and peptide analog synthesis. The molecule contains a free amino group and a carboxyl group characteristic of amino acids, with the aromatic naphthyl moiety providing a hydrophobic, π-rich side-chain functionality for spectroscopic labeling, binding studies, and conformational effects in peptide contexts. As a defined amino acid building block, it is employed in solution-phase or solid-phase peptide synthesis and in chemical biology workflows where an extended aromatic chromophore or side-chain mimic is incorporated to probe molecular recognition, aggregation tendencies, or structure-activity relationships.
CAT No: CP22202
CAS No:55516-54-6
Synonyms/Alias:Z-DAB(Z)-OH;55478-23-4;AC1OLRAK;Z-DAB-OH;(2S)-2,4-bis(phenylmethoxycarbonylamino)butanoicAcid;CTK8G1595;ZINC4899657;7871AH;(S)-2,4-Bis(carbobenzoxyamino)butyricacid;Nalpha,gamma-Bis-Z-L-2,4-diaminobutyricacid;K-9908
3-(1-Naphthyl)-L-Alanine is an L-amino acid bearing a 1-naphthyl substituent on the side chain, providing a rigid, hydrophobic aromatic moiety that is commonly leveraged in chemical biology and peptide/peptidomimetic design. As a non-proteinogenic aromatic amino acid building block, it offers a convenient handle for introducing a bulky aryl group into synthetic peptides, structure-property studies, and binding or folding assays. Its stereodefined amino acid backbone makes it practical for downstream coupling workflows where side-chain aromaticity and steric effects are key variables.
1. Peptide Building Block Use
3-(1-Naphthyl)-L-Alanine is used by peptide chemistry groups to incorporate a 1-naphthyl side chain into custom peptides and peptidomimetics for structure-activity and structure-property investigations. The aromatic naphthalene group enables researchers to probe how hydrophobic and π-surface characteristics influence conformation, aggregation propensity, and intermolecular interactions in synthetic peptide systems. This building block is also frequently selected when a single, well-defined aromatic substituent is needed to create a consistent steric and electronic environment across peptide analog series.
2. Medicinal Chemistry SAR Probes
3-(1-Naphthyl)-L-Alanine supports medicinal chemistry workflows focused on SAR (structure-activity relationship) refinement of peptide-like or peptidomimetic scaffolds. Teams developing ligand series often use this aromatic amino acid to introduce a bulky hydrophobic aryl element that can modulate binding pocket complementarity and shape recognition in receptor/target binding studies. Because the naphthyl side chain is chemically stable and strongly hydrophobic, it is commonly employed as a controlled substituent for comparing analogs where aromatic size and lipophilicity are systematically varied.
3. Chemical Biology Interaction Studies
3-(1-Naphthyl)-L-Alanine is applied in chemical biology to generate synthetic probes and interaction-mapping reagents where an aromatic side chain is used to drive or report on noncovalent interactions. Researchers incorporate this building block into peptide fragments used in binding assays, competition experiments, and affinity-mimicking constructs, taking advantage of the naphthalene's strong hydrophobic and π-interaction potential. In such workflows, the defined L-amino acid stereochemistry helps maintain consistent backbone geometry while the naphthyl group provides a reproducible aromatic interaction motif.
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