Boc-3-(2-Naphthyl)-L-Alanine is a Boc-protected, L-configured amino acid derivative belonging to the alanine family, featuring a side chain substituted at the 3-position with a 2-naphthyl group. The molecule contains a free carboxylic acid and an N-Boc carbamate that masks the amino functionality, while the bulky aromatic naphthyl substituent provides a hydrophobic, π-rich side-chain surface for conformational and interaction studies. In peptide and amide synthesis workflows, this protected amino acid is used as a building block to introduce the naphthyl-bearing alanine residue into peptide analogues and to support structure-activity or binding studies through controlled side-chain presentation.
CAT No: CP22210
CAS No:58438-04-3
Synonyms/Alias:3-(2-Naphthyl)-L-alanine;58438-03-2;(S)-2-Amino-3-(naphthalen-2-yl)propanoicacid;BETA-(2-NAPHTHYL)-ALANINE;L-3-(2-Naphthyl)-alanine;SBB065833;(2S)-2-amino-3-(2-naphthyl)propanoicacid;(2S)-2-amino-3-naphthalen-2-ylpropanoicacid;(s)-2-amino-3-naphthalen-2-yl-propionicacid;6960-34-5;NAL;L-3-(2-NAPHTHYL)ALANINE;l-2-naphthylalanine;PubChem17989;H-2-Nal-OH?HCl;AC1L4HRJ;UNII-W425Q6KV9R;SCHEMBL93303;KSC495S1F;W425Q6KV9R;CTK3J5912;JPZXHKDZASGCLU-LBPRGKRZSA-N;MolPort-001-758-758;ZINC128256;ANW-32944
Boc-3-(2-Naphthyl)-L-Alanine is a Boc-protected amino acid building block featuring the L-stereochemistry and a bulky 2-naphthyl side chain that strongly influences sterics and hydrophobic character. The N-terminal Boc group makes it directly compatible with protected-amino-acid handling workflows commonly used for peptide fragment assembly, while the aromatic side chain supports incorporation into hydrophobic and π-interaction-rich sequences. This reagent is frequently selected when researchers need a stable, isolable amino acid intermediate that can be carried through peptide coupling steps to deliver naphthyl-substituted motifs.
1. Hydrophobic Peptide Building Block
Boc-3-(2-Naphthyl)-L-Alanine is used by peptide chemists to introduce a naphthyl-containing residue into custom peptide sequences, enabling hydrophobic packing and aromatic side-chain interactions that are often important for folding, binding-site mimicry, and structure-activity relationship studies. The Boc protection at the amino terminus supports its role as a defined, single-residue component for stepwise synthesis of peptide fragments, where controlled protection and side-chain identity are required for reproducible coupling outcomes. Research groups building receptor-binding peptides, membrane-interacting peptide analogs, and aromatic-rich peptidomimetics rely on this specific naphthyl side chain to tune lipophilicity and conformational preferences without changing the backbone framework.
2. Peptidomimetic And SAR Intermediates
Boc-3-(2-Naphthyl)-L-Alanine is also employed in medicinal chemistry programs that develop peptidomimetics and non-natural peptide analogs, particularly when aromatic substituents are used to probe binding pocket shape and π-interaction contributions. The 2-naphthyl substituent provides a larger aromatic surface than simple phenylalanine-like side chains, which can be leveraged to map hydrophobic contact points and refine lead structures. Pharmaceutical intermediate development teams frequently use this Boc-protected amino acid as a standardized building block for assembling modified peptide fragments that later feed into larger coupling sequences, allowing SAR libraries to be generated with consistent stereochemical and side-chain features.
3. Protected Amino Acid Fragment Synthesis
Boc-3-(2-Naphthyl)-L-Alanine is well suited for protected-amino-acid fragment condensation workflows where the N-terminal Boc group is maintained through intermediate handling and coupling steps. In custom peptide manufacturing and academic peptide synthesis, the reagent's defined protection pattern and stable aromatic side chain help ensure that the naphthyl residue is introduced with minimal ambiguity in sequence assembly. This makes it a practical choice for constructing peptide segments that will be further elaborated, including longer-chain targets where steric bulk from the naphthyl group requires careful selection of building blocks to preserve sequence fidelity during stepwise synthesis.
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