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Specifications
| Appearance | White powder |
| Purity (HPLC) | 98% min |
| Optical Purity | 0.5% max L-enantiomer |
| Specific Rotation [α]20 D | +20° ± 4° (C=1 in DMF) |
| Clarity of Solution | 0.3 g in 2 mL DMF clear solution |
| Water Content (K.F.) | 2.0% max |
| Loss on Drying | 5.0% max (40°C, 2h) |
| IR Spectrum | In accordance with the structure |
| Mass Spectrum | In accordance with the structure |
| NMR Spectrum | In accordance with the structure |
Applications
Fmoc-D-Trp(Boc)-OH (CAS 163619-04-3) is a protected amino acid derivative widely used in peptide synthesis and medicinal chemistry. It serves as a building block for the solid-phase synthesis of peptides containing D-tryptophan residues, where the Fmoc (9-fluorenylmethoxycarbonyl) group protects the amino terminus and the Boc (tert-butoxycarbonyl) group protects the indole side chain. This dual protection allows for selective deprotection and sequential peptide chain elongation, making it essential in the preparation of bioactive peptides, therapeutic peptides, and peptide-based probes. It is also utilized in the synthesis of peptidomimetics and complex molecules for drug discovery and biochemical research.
Benefits
The benefits of Fmoc-D-Trp(Boc)-OH stem from its dual protection strategy and stereochemical integrity. The Fmoc group provides mild base-labile protection for the amino group, facilitating efficient solid-phase peptide synthesis, while the Boc group safeguards the reactive indole side chain during multi-step reactions. The D-configuration of tryptophan ensures incorporation of stereochemically defined residues, enabling precise control over peptide structure and biological activity. Its chemical stability, solubility in common organic solvents, and compatibility with standard coupling reagents make it a reliable intermediate for automated and manual peptide synthesis.
Conclusion
Fmoc-D-Trp(Boc)-OH is a crucial protected amino acid used in peptide synthesis and medicinal chemistry. Its dual protection and stereochemical precision allow for efficient incorporation of D-tryptophan into bioactive peptides and peptidomimetics. By providing stability, selectivity, and synthetic versatility, it remains an essential building block in modern peptide research, drug discovery, and biochemical applications.
