Boc-3-(1-Naphthyl)-D-Alanine is a protected, non-natural amino acid derivative featuring a D-amino acid backbone bearing a 3-(1-naphthyl) substituted side chain and an N-terminal Boc (tert-butoxycarbonyl) protecting group. The molecule contains both an amino functionality that is masked as the Boc carbamate and a carboxylic acid group, with the bulky hydrophobic naphthyl substituent providing aromatic character for hydrophobic and π-interaction studies. In peptide and amide synthesis workflows, the Boc protection supports chemoselective stepwise coupling at the carboxyl group while the aryl side chain can be incorporated as a structural motif for structure-activity investigations, fluorescent or binding-probe design, and preparation of more complex amino acid and peptide derivatives.
CAT No: CP22203
CAS No:76932-48-4
Synonyms/Alias:76932-48-4;Boc-D-1-Nal-OH;BOC-D-1-NAPHTHYLALANINE;Boc-3-(1-naphthyl)-D-alanine;N-(tert-Butoxycarbonyl)-3-(1-naphthyl)-D-alanine;(R)-2-((tert-Butoxycarbonyl)amino)-3-(naphthalen-1-yl)propanoicacid;(R)-N-Boc-D-(1-naphthyl)alanine;Boc-D-3-(1-Naphthyl)-alanine;N-Boc-3-(1-naphthyl)-D-alanine;SBB067207;3-(NAPHTHALEN-1-YL)-N-BOC-D-ALANINE;(2R)-2-[(tert-butoxy)carbonylamino]-3-naphthylpropanoicacid;(2R)-2-[(tert-butoxycarbonyl)amino]-3-naphthalen-1-ylpropanoicacid;(R)-2-TERT-BUTOXYCARBONYLAMINO-3-NAPHTHALEN-1-YL-PROPIONICACID;PubChem11936;AC1MC1A6;BOC-D-NAL(1)-OH;KSC491O8P;15045_ALDRICH;SCHEMBL4600435;BOC-D-ALA(1-NAPH)-OH;15045_FLUKA;CTK3J1787;MolPort-001-758-474;BOC-D-ALA(1-NAPHTHYL)-OH
Boc-3-(1-Naphthyl)-D-Alanine is a D-configured, non-proteinogenic amino acid building block protected at the amino group with a Boc (tert-butoxycarbonyl) group and bearing a bulky 1-naphthyl substituent at the 3-position. This aromatic side-chain makes the residue a useful chiral scaffold for constructing sterically defined peptidomimetic motifs and hydrophobic/aromatic pharmacophore elements. In peptide synthesis workflows, its protected form supports stepwise assembly into protected peptide segments and downstream conversion into larger intermediates.
1. Peptidomimetic Building Block
Boc-3-(1-Naphthyl)-D-Alanine is used by medicinal chemistry and peptide-chemistry groups to introduce a D-amino acid motif bearing a 1-naphthyl aromatic group into peptidomimetics and constrained analogs. The combination of D-stereochemistry and the rigid, hydrophobic naphthyl substituent helps researchers build structure-activity relationship (SAR) series where aromatic surface area and stereochemical presentation are key design variables. The Boc protection supports incorporation into protected peptide segments during custom synthesis campaigns, enabling rapid generation of analog libraries for hit-to-lead optimization and SAR mapping.
2. Protected Residue For Peptide Assembly
Boc-3-(1-Naphthyl)-D-Alanine serves as a protected amino acid residue for solution-phase or segment condensation strategies where a Boc-protected, chiral building block is required. Peptide synthesis teams commonly select Boc-protected amino acid derivatives when they want controlled handling of the amino functionality during stepwise assembly and when they plan to continue coupling into longer protected sequences or advanced intermediates. The naphthyl side chain also provides a chemically robust aromatic handle for incorporating hydrophobic character into peptide-like scaffolds without introducing additional reactive side-chain groups that could complicate downstream coupling steps.
3. Chiral Intermediate For SAR Libraries
Boc-3-(1-Naphthyl)-D-Alanine is frequently employed in pharmaceutical intermediate development to prepare chiral, aromatic-containing fragments used in SAR library synthesis. Research groups developing peptidomimetic candidates often rely on D-configured amino acid building blocks to systematically vary backbone stereochemistry while maintaining a consistent aromatic pharmacophore element. The resulting intermediates support parallel synthesis of analogs where the 1-naphthyl group is retained as a defining structural feature, while other positions are diversified to probe structure-property relationships in lead optimization programs.
4. Aromatic Pharmacophore Incorporation
Boc-3-(1-Naphthyl)-D-Alanine is a practical choice for incorporating an extended aromatic (naphthyl) motif into peptide-like frameworks used in chemical biology tool development and ligand design. Teams constructing binding-focused scaffolds often need a residue that contributes both hydrophobic bulk and a rigid aromatic surface, and the 1-naphthyl substituent provides that contribution without relying on additional functional groups for the aromatic interaction component. By using this protected chiral building block, researchers can position the aromatic element within a defined sequence context, supporting the preparation of structured ligands and peptidomimetic probes used for mechanistic studies and molecular recognition optimization.
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