Boc-3-Fluoro-D-Phenylalanine is a protected, non-natural amino acid derivative featuring a D-phenylalanine backbone bearing a fluorine substituent at the 3-position of the aromatic ring and an N-terminal Boc (tert-butoxycarbonyl) protecting group. The molecule contains a free carboxylic acid functional group and a Boc-protected amino group, with the aryl side chain incorporating a 3-fluoro substituent that modulates electronic and steric properties relative to unmodified phenylalanine. As a stepwise peptide-synthesis building block, the Boc protection supports chemoselective coupling at the carboxyl and amino termini while the fluorinated aromatic side chain provides a handle for structure-activity studies, analytical method development, and incorporation of fluorinated residues into synthetic peptides.
CAT No: CP14505
CAS No:114873-11-9
Synonyms/Alias:114873-11-9;Boc-3-fluoro-D-phenylalanine;(R)-N-Boc-3-Fluorophenylalanine;Boc-D-Phe(3-F)-OH;(R)-2-((TERT-BUTOXYCARBONYL)AMINO)-3-(3-FLUOROPHENYL)PROPANOICACID;MFCD00672523;(2R)-2-[(tert-butoxycarbonyl)amino]-3-(3-fluorophenyl)propanoicacid;Boc-L-phe(3-F)-OH;BOC-3-FLUORO-L-PHE;AmbotzBAA1366;BOC-D-3-Fluorophe;Boc-3-fluoro-D-Phe;AC1ODU0M;14995_ALDRICH;SCHEMBL1269412;14995_FLUKA;CTK8A9283;MolPort-001-776-374;EBD28413;ZINC2567676;ANW-16719;CB-730;AKOS015836560;AC-5830;CS13526
Boc-3-Fluoro-D-Phenylalanine is a D-configured fluorinated phenylalanine derivative equipped with a Boc (tert-butoxycarbonyl) protecting group on the amino functionality, making it a bench-stable, protected amino acid building block for peptide and peptidomimetic synthesis. The 3-fluoro substituent on the aromatic ring provides a defined electronic and steric handle that is frequently leveraged in medicinal chemistry programs to probe structure-activity relationships and improve analog design. As a protected amino acid, it is typically handled as a synthetic intermediate that can be incorporated into protected peptide segments under controlled coupling workflows.
1. Peptide Building Blocks
Boc-3-Fluoro-D-Phenylalanine is used by peptide chemistry groups to construct D-amino acid-containing sequences where stereochemical inversion is required for conformational control or protease selectivity studies. The Boc protection supports routine peptide assembly workflows by keeping the amino group masked during segment preparation, while the fluorinated aromatic side chain serves as a chemically defined analog of phenylalanine for SAR-focused library synthesis. In practice, researchers select this building block when they need a single, well-defined fluorinated residue to be introduced site-specifically into short peptides, cyclic peptides, or peptidomimetic scaffolds.
2. Medicinal Chemistry SAR Analogues
Boc-3-Fluoro-D-Phenylalanine is commonly directed to medicinal chemistry synthesis campaigns that require fluorinated, D-configured amino acid motifs as part of lead optimization. The aryl fluorine at the 3-position offers a targeted modification that can influence physicochemical properties and interaction patterns in binding-site studies, enabling chemists to rapidly generate analog series around a D-amino acid pharmacophore. Development teams and CROs use this reagent to prepare defined intermediates that feed into larger peptide-drug or peptidomimetic structures, where the ability to introduce a specific 3-fluoro substitution is critical for interpretable SAR outcomes.
3. Protected Intermediate For Peptidomimetics
Boc-3-Fluoro-D-Phenylalanine is also used as a protected amino acid intermediate for downstream synthesis of fluorinated peptidomimetics and specialized amino acid derivatives. The combination of Boc protection and the fluorinated aromatic side chain makes it a practical starting material for assembling larger fragments while maintaining functional-group compatibility through multi-step synthetic sequences. Pharmaceutical intermediate development teams rely on such protected, stereodefined amino acid derivatives to ensure that the D-configuration and the 3-fluoro substitution remain intact through fragment coupling and purification steps prior to final scaffold assembly.
4. Analytical Reference Material Development
Boc-3-Fluoro-D-Phenylalanine is frequently incorporated into analytical method development workflows where defined fluorinated amino acid standards or internal reference materials are needed to support LC-MS or related characterization of peptide intermediates. Researchers use the protected, stereodefined form to track specific building-block incorporation during synthesis and to validate identity for fluorinated D-amino acid-containing fragments. This use is particularly relevant when distinguishing closely related aromatic analogues in complex reaction mixtures, where the presence of the 3-fluorine substituent provides a clear chemical signature for analytical confirmation.
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