L-N-Boc-5-fluorotryptophan contains a fluorinated indole ring that alters electron distribution and stacking interactions. The Boc group stabilizes the amino function during synthesis. Researchers use it to explore modified fluorescence behavior and solvent-driven conformational changes. Its structure supports constrained aromatic environments.
CAT No: R2171
CAS No:53478-53-8
Synonyms/Alias:53478-53-8;L-N-BOC-5-FLUOROTRYPTOPHAN;BOC-5-FLUORO-L-TRYPTOPHAN;(S)-2-((tert-Butoxycarbonyl)amino)-3-(5-fluoro-1H-indol-3-yl)propanoic acid;(2S)-3-(5-fluoro-1H-indol-3-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid;(2S)-2-{[(tert-butoxy)carbonyl]amino}-3-(5-fluoro-1H-indol-3-yl)propanoic acid;MFCD09264333;Boc-Trp(5-F)-OH;L-Tryptophan, N-[(1,1-dimethylethoxy)carbonyl]-5-fluoro-;(2S)-2-[(TERT-BUTOXYCARBONYL)AMINO]-3-(5-FLUORO-1H-INDOL-3-YL)PROPANOIC ACID;Boc-L-Trp(5-F)-OH;SCHEMBL8939508;DTXSID40569641;AKOS015904115;AS-73248;A50267;N-(tert-Butoxycarbonyl)-5-fluoro-L-tryptophan;L-N-Boc-5-fluorotryptophan (Boc-L-Trp(5-F)-OH);(S)-2-((tert-Butoxycarbonyl)amino)-3-(5-fluoro-1H-indol-3-yl)propanoicacid;
L-N-Boc-5-fluorotryptophan is a synthetic, N-Boc-protected, fluorinated derivative of the natural amino acid tryptophan. Featuring a fluorine atom at the 5-position of the indole ring and a tert-butyloxycarbonyl (Boc) group protecting the α-amino function, this compound is designed for advanced research applications in peptide chemistry, protein engineering, and molecular biology. Its unique structure enables the incorporation of a fluorine atom into peptide chains or proteins, providing a valuable tool for probing molecular interactions, modulating biochemical properties, and facilitating analytical detection. The presence of the Boc group enhances its utility in solid-phase peptide synthesis by offering controlled deprotection and improved handling characteristics.
Peptide Synthesis: L-N-Boc-5-fluorotryptophan is widely used as a building block in solid-phase and solution-phase peptide synthesis, enabling the site-specific introduction of a fluorinated tryptophan residue into custom peptide sequences. The Boc protection on the α-amino group allows for selective deprotection under mild acidic conditions, reducing side reactions and facilitating efficient chain elongation. Incorporating a 5-fluoro substituent into peptides can modulate their electronic and steric properties, which is especially useful for structure-activity relationship studies and the development of peptide-based probes.
Protein Engineering: The fluorinated tryptophan analog serves as a powerful tool for protein engineering and mutagenesis studies. By substituting native tryptophan residues with 5-fluorotryptophan during recombinant protein expression or chemical synthesis, researchers can investigate the effects of fluorine substitution on protein folding, stability, and function. The altered electronic environment at the indole ring can influence protein-ligand interactions, providing insight into the role of aromatic residues in biological recognition processes.
Spectroscopic Analysis: The introduction of a fluorine atom into tryptophan residues enables the use of 19F nuclear magnetic resonance (NMR) spectroscopy for sensitive, site-specific monitoring of peptides and proteins. 5-fluorotryptophan imparts a unique NMR signal that is free from background interference in biological samples, allowing researchers to study conformational changes, binding events, and dynamic processes with high specificity. This application is particularly valuable for elucidating the structural dynamics of complex biomolecules in solution.
Enzyme Mechanism Studies: Incorporation of the fluorinated analog into substrate peptides or proteins can be used to probe enzyme-substrate interactions and catalytic mechanisms. The presence of a fluorine atom at the 5-position can subtly alter substrate recognition or reactivity, providing mechanistic insight into the role of tryptophan residues in enzymatic processes. This approach is instrumental in dissecting the contributions of aromatic side chains to catalysis and binding in a variety of enzyme systems.
Analytical Method Development: L-N-Boc-5-fluorotryptophan is also utilized as a reference standard or internal control in analytical chemistry, particularly in the development and validation of chromatographic or mass spectrometric methods for amino acid and peptide analysis. The unique mass and chemical properties conferred by fluorination and Boc protection facilitate unambiguous detection and quantitation, supporting rigorous analytical workflows in peptide research and quality control environments.
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