Boc-Pentafluoro-L-Phenylalanine is a Boc-protected, L-configured phenylalanine derivative in which the aromatic side chain bears multiple fluorine substituents (pentafluoro-substituted phenyl ring). The molecule contains a Boc-protected α-amino group and a free carboxylic acid, and its fluorinated benzyl side chain provides a strongly electron-withdrawing aromatic functionality that can affect peptide conformation and chemical reactivity during synthesis. In peptide chemistry, this protected amino acid is used as a building block for introducing a fluorinated phenylalanine residue into peptides or peptide intermediates, supporting stepwise assembly while the Boc group helps control chemoselectivity at the amino functionality.
CAT No: CP16204
CAS No:34702-60-8
Synonyms/Alias:Boc-L-Pentafluorophenylalanine;34702-60-8;(S)-2-((tert-Butoxycarbonyl)amino)-3-(perfluorophenyl)propanoicacid;BOC-L-PENTAFLUOROPHE;Boc-L-2,3,4,5,6-Pentafluorophenylalanine;(2S)-2-[(tert-butoxycarbonyl)amino]-3-(pentafluorophenyl)propanoicacid;BOC-1,2,3,4,5-PENTAFLUORO-L-PHENYLALANINE;L-Pentafluorophenylalanine,N-BOCprotected;Boc-Phe(5F)-OH;BOC-PHE(F5)-OH;BOC-L-PHE(F5)-OH;BOC-PENTAFLUORO-PHE-OH;BOC-PENTAFLUORO-L-PHE-OH;CTK8F0558;MolPort-001-775-412;ZINC2517129;CB-770;AKOS015908004;AB04022;AC-5837;BL136-1;N-BOC-L-PENTAFLUOROPHENYLALANINE;VA50082;VA50146;AK163682
Boc-Pentafluoro-L-Phenylalanine is a Boc-protected, fluorinated phenylalanine derivative designed for peptide and medicinal chemistry workflows where strong electron-withdrawing side-chain character is valuable. The pentafluorinated aromatic ring provides distinctive physicochemical properties that are frequently leveraged in structure-property studies, while the Boc protection supports controlled incorporation into protected peptide segments during synthesis. This reagent is commonly selected by peptide chemists and process developers building fluorinated analogs for downstream biological, biophysical, and analytical characterization.
1. Peptide Synthesis Building Block
Boc-Pentafluoro-L-Phenylalanine is used as a protected amino acid building block for assembling fluorinated peptide segments in custom peptide synthesis and peptide library workflows. The Boc-protected amino functionality supports reliable coupling strategies in protected-segment construction, enabling incorporation of a pentafluorinated phenylalanine residue at defined positions within peptides. Researchers often choose this residue to introduce a highly fluorinated aromatic side chain that can alter local polarity, aromatic interactions, and conformational preferences, which is useful when comparing peptide analogs in structure-activity or structure-property programs.
2. Medicinal Chemistry Fluorinated Analog Development
Boc-Pentafluoro-L-Phenylalanine is frequently employed in medicinal chemistry and peptidomimetic development to access fluorinated analogs where the pentafluoroaryl group serves as a tunable modulator of electronic effects and aromatic character. Medicinal chemistry groups use this building block to prepare intermediate fragments that later feed into peptide-like scaffolds, constrained analogs, or fluorinated conjugates used in SAR studies. The Boc-protected form supports stepwise synthesis of defined fragments, allowing developers to introduce the pentafluorinated aromatic motif with positional control before final assembly and purification.
3. Pharmaceutical Intermediate Synthesis
Boc-Pentafluoro-L-Phenylalanine is also used as a pharmaceutical intermediate for manufacturing fluorinated amino acid derivatives and related protected fragments for downstream coupling chemistry. Process and development chemists select this reagent when a pentafluorinated phenylalanine motif is required as a key intermediate element, such as in the preparation of protected building blocks for larger synthetic sequences. The combination of Boc protection and the pentafluoroaryl side chain supports consistent handling in intermediate workflows where controlled functional-group availability and reproducible downstream reactivity are important for scale-up and custom synthesis.
4. Analytical Reference Compound Production
Boc-Pentafluoro-L-Phenylalanine is used in analytical method development and reference material preparation for studies involving fluorinated amino acid motifs. Analytical chemistry teams incorporate this type of protected, fluorinated amino acid derivative into calibration or characterization workflows for LC-MS-based assays that target fluorinated peptide fragments or fluorinated building blocks. The pentafluoroaryl group provides a distinctive mass signature that can improve traceability of the motif during impurity profiling, fragment identification, and method verification for fluorinated peptide and intermediate analytics.
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