Boc-2-Fluoro-L-Phenylalanine is a protected amino acid derivative of L-phenylalanine in which the alpha-amino group is protected as a Boc (tert-butoxycarbonyl) carbamate and a fluorine substituent is present at the 2-position relative to the carboxylate. The molecule contains a Boc-protected amino functionality and a free carboxylic acid, while the side chain remains a benzyl group bearing a fluorinated alpha-carbon that can influence steric and electronic properties compared with the corresponding non-fluorinated analogue. In peptide and amino acid derivative synthesis, this protected fluorinated building block is employed to introduce a 2-fluoro-substituted phenylalanine residue with controlled chemoselectivity during stepwise coupling and subsequent deprotection to enable incorporation into larger peptide structures or structure-activity studies.
CAT No: CP14404
CAS No:114873-00-6
Synonyms/Alias:114873-00-6;Boc-L-2-Fluorophenylalanine;Boc-Phe(2-F)-OH;BOC-L-2-Fluorophe;Boc-2-fluoro-L-phenylalanine;Boc-D-2-fluorophenylalanine;(S)-2-((tert-Butoxycarbonyl)amino)-3-(2-fluorophenyl)propanoicacid;(S)-N-BOC-2-FLUOROPHENYLALANINE;SBB066163;Boc-L-phe(2-F)-OH;(2S)-2-[(tert-butoxy)carbonylamino]-3-(2-fluorophenyl)propanoicacid;(2S)-2-[(tert-butoxycarbonyl)amino]-3-(2-fluorophenyl)propanoicacid;186431-96-9;PubChem6121;Boc-2-Fluoro-L-Phe-OH;AC1MC19O;BOC-2-FLUORO-L-PHE;15024_ALDRICH;BOC-O-FLUORO-L-PHE-OH;N-Boc-o-fluoro-L-phenylalanine;SCHEMBL1270141;BOC-L-2-FLUORO-PHE-OH;15024_FLUKA;MolPort-001-771-176;NTWUXBKUDXGMHV-NSHDSACASA-N
Boc-2-Fluoro-L-Phenylalanine is a Boc-protected L-phenylalanine analog bearing a fluorine substituent at the alpha (2-) position. This combination of an N-terminal protecting group and a stereodefinable, fluorinated amino acid side-chain/α-substitution makes it a valuable building block for incorporating fluorine into peptides and peptidomimetic structures. In medicinal chemistry and chemical biology workflows, fluorinated amino acid residues are frequently used to probe structure-property relationships, modulate physicochemical behavior, and support mechanistic studies where the presence of fluorine provides a distinct analytical handle.
1. Fluorinated Peptide Synthesis
Boc-2-Fluoro-L-Phenylalanine is used as an amino acid building block for custom peptide synthesis where incorporation of an α-fluorinated phenylalanine residue is desired. Peptide chemists select this protected form to enable stepwise assembly with an N-terminal Boc strategy, while the fluorine at the 2-position remains intact through the coupling workflow, allowing downstream peptide purification and characterization to retain the fluorinated motif. This reagent is particularly relevant for preparing fluorinated peptide standards, SAR-focused peptide libraries, and mechanistic peptide probes used in biochemical assay development and protein interaction studies.
2. Medicinal Chemistry SAR Probes
Boc-2-Fluoro-L-Phenylalanine supports medicinal chemistry programs that require fluorine-substituted amino acid motifs as part of peptidomimetic or constrained peptide-like scaffolds. Medicinal chemistry groups use this building block to introduce a fluorinated stereocenter within a residue that otherwise resembles phenylalanine, enabling systematic evaluation of how fluorination influences conformation, local polarity, and metabolic/chemical stability trends in lead optimization campaigns. The Boc-protected amino acid format streamlines incorporation into synthetic sequences that generate fluorinated intermediates and final bioactive scaffold candidates for in vitro characterization.
3. Chemical Biology Structure Studies
Boc-2-Fluoro-L-Phenylalanine is frequently employed in chemical biology to generate fluorine-containing peptides used for structure-function investigations and interaction mapping. Researchers use fluorinated residues as a distinct chemical tag that can be monitored by NMR and mass spectrometry workflows, supporting experiments where residue-level labeling improves interpretability of binding or conformational readouts. The protected amino acid format helps ensure consistent residue incorporation during peptide construction, which is important when comparing closely related analogs that differ only by the presence and position of the fluorine substituent.
4. Pharmaceutical Intermediate Development
Boc-2-Fluoro-L-Phenylalanine is also used as a pharmaceutical intermediate building block for downstream synthesis of fluorinated amino acid derivatives and peptide-related intermediates. Process and development chemists rely on the Boc protection to manage reactivity during multi-step manufacturing routes that require controlled functional group handling before final deprotection or further derivatization. This makes the reagent a practical starting point for preparing fluorinated coupling partners and protected fluorinated fragments used in the iterative assembly of fluorinated lead structures and related research materials.
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