CAS · 138774-94-4
Product Overview
(R)-N-Fmoc-2-Naphthylalanine is a high-purity biochemical-reagents supplied for industrial and specialty chemical applications. Contact our team for specifications, packaging options and lead times.
Product Specifications
| Appearance: | White to off-white powder |
|---|---|
| Purity (HPLC): | 98% min |
| TLC: | 98% min |
| Optical Rotation: | +15° ± 3° (C=1 in DMF) |
| Element Analysis (C,H,N): | 5% max |
| Clarity of Solution: | 0.3 g in 2 mL DMF, clear solution |
| Water Content (K.F.): | 2% max |
| Loss on Drying: | 2% max |
| IR: | In accordance with the structure |
| Mass: | In accordance with the structure |
| NMR: | In accordance with the structure |
Applications
(R)-N-Fmoc-2-Naphthylalanine is primarily used as a protected chiral amino acid building block in peptide synthesis and medicinal chemistry. The Fmoc (9-fluorenylmethyloxycarbonyl) group enables temporary protection of the amine functionality, allowing selective reactions at the carboxyl group while preserving the stereochemistry of the naphthylalanine residue. It is extensively applied in solid-phase peptide synthesis (SPPS) to incorporate aromatic, hydrophobic side chains into peptides, enhancing structural stability, hydrophobic interactions, and biological activity. In pharmaceutical research, it is used to design peptidomimetics, enzyme inhibitors, and receptor modulators with defined three-dimensional structures. Additionally, it serves in the development of fluorescent or hydrophobic peptide probes due to the naphthyl moiety, aiding in molecular recognition studies, protein labeling, and bioassays.
Benefits
The compound offers high chiral purity, ensuring stereochemically precise incorporation into peptide sequences, which is crucial for maintaining biological activity and folding patterns. The Fmoc-protection allows compatibility with a wide range of peptide coupling reagents and deprotection conditions, improving synthetic efficiency and yield. The naphthyl side chain provides hydrophobicity and aromaticity, enhancing peptide stability, binding affinity, and structural rigidity. Its chemical stability and solubility in common organic solvents make it versatile for diverse synthetic protocols. Overall, it enables the design of peptides and peptidomimetics with enhanced pharmacological properties, structural diversity, and functional performance in research and drug discovery.
Conclusion
(R)-N-Fmoc-2-Naphthylalanine is a vital chiral amino acid intermediate for peptide synthesis, medicinal chemistry, and biochemical research. Its Fmoc protection, stereochemical integrity, and aromatic side chain allow efficient, high-quality synthesis of bioactive peptides, peptidomimetics, and molecular probes, supporting innovation in drug development and peptide-based applications.
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