Fmoc-2,5-Difluoro-L-Phenylalanine is an Fmoc-protected, L-phenylalanine-derived amino acid bearing two fluorine atoms at the 2- and 5-positions of the phenyl side chain, placing it in the class of fluorinated, non-unmodified side-chain substituted amino acids used for peptide chemistry. The molecule contains a free carboxyl group and an amino group masked by the Fmoc (9H-fluoren-9-ylmethoxycarbonyl) protecting group, while the difluorinated aromatic ring provides altered hydrophobicity and electronic character relative to unsubstituted phenylalanine. In synthesis, it functions as a protected amino acid building block for stepwise incorporation into peptides via protected-amino-acid coupling strategies, and its fluorinated aromatic motif can be used in structure-activity studies, chemical biology labeling contexts, and analytical method development where fluorine-containing side chains improve detectability or enable NMR/fluorine-specific readouts.
CAT No: CP12806
Fmoc-2,5-Difluoro-L-Phenylalanine is an Fmoc-protected L-phenylalanine derivative bearing two fluorine atoms on the aromatic ring at the 2- and 5-positions, creating a rigid, electronically modulated side chain while preserving the stereogenic center of the amino acid. The molecule contains an N-(9H-fluoren-9-ylmethoxycarbonyl) protecting group on the amino functionality and an activated carboxylate handle as part of the amino acid scaffold, enabling controlled peptide coupling after deprotection. The presence of aryl fluorides introduces distinctive reactivity patterns for subsequent derivatization and can influence conformational preferences and binding interactions in peptide and peptidomimetic contexts. As a chiral, protected amino acid building block, it functions as a fluorinated aromatic intermediate suited to peptide synthesis, SAR-driven molecular design, and downstream chemical modification.
1. Peptide Synthesis
Fmoc-2,5-Difluoro-L-Phenylalanine is applied in solid-phase peptide synthesis and solution-phase peptide assembly where the Fmoc group supports standard N-terminal protection and orthogonal deprotection strategies. The L-configuration at the alpha carbon provides stereochemical fidelity for backbone incorporation, while the difluorinated phenyl side chain supplies a defined aromatic motif that can be carried through coupling steps without altering the stereocenter. The aryl fluorines can remain intact during peptide construction, enabling later side-chain functionalization or serving as stable halogen substituents for structure-activity relationship studies. Fluorinated aromatic residues introduced via this protected amino acid can be used to generate peptide libraries for binding-site probing and to tune physicochemical properties relevant to peptide science.
2. Peptidomimetics And SAR
Fmoc-2,5-Difluoro-L-Phenylalanine serves chemical biology and medicinal chemistry workflows focused on peptidomimetics and structure-activity relationship studies. The difluoro-substituted phenyl ring provides a stereochemically defined aromatic pharmacophore whose electronic and steric characteristics may be leveraged to modulate molecular recognition in peptide analogs. The Fmoc-protected amino acid format allows incorporation into designed sequences, generating analogs where fluorine substitution patterns are systematically varied while maintaining consistent backbone stereochemistry. The resulting fluorinated peptide fragments can act as scaffolds for SAR mapping, fragment optimization, and iterative design of amino-acid-derived ligands.
3. Side-Chain Functionalization
Fmoc-2,5-Difluoro-L-Phenylalanine is suitable for downstream side-chain functionalization chemistry where aryl fluorides act as handles for substitution or cross-coupling strategies after peptide or fragment assembly. The protected amino acid structure permits stepwise synthesis: Fmoc removal and peptide coupling can be performed while the difluoro aromatic ring remains a chemically addressable motif for later transformation. The fluorine atoms at distinct positions on the phenyl ring enable regio-defined derivatization pathways, supporting the preparation of new analogs such as substituted aryl variants or conjugation-ready intermediates. This design supports synthetic organic chemistry routes that connect amino acid derivatization with scalable intermediate generation for fine chemical and research-grade library production.
4. Chemical Biology Labeling
Fmoc-2,5-Difluoro-L-Phenylalanine can be used in chemical biology research requiring fluorinated amino acid incorporation into probes and tagged peptide constructs. The Fmoc-protected amine enables controlled assembly into peptides that maintain a defined stereochemical and aromatic environment, which can influence binding and localization of the resulting probe. The difluoro phenyl side chain can function as a stable, chemically robust motif for spectroscopic tracking or for tuning interactions without introducing reactive groups during synthesis. The ability to introduce a defined fluorinated residue supports biomolecule modification strategies that generate labeled peptide tools for studying molecular interactions and pathway-relevant recognition events.
5. Pharmaceutical Manufacturing Intermediate
Fmoc-2,5-Difluoro-L-Phenylalanine is relevant to pharmaceutical manufacturing and process chemistry as a protected amino acid intermediate for producing fluorinated peptide building blocks at scale. The Fmoc protection strategy supports reliable N-protection during handling and downstream coupling operations, aligning with industrially practiced peptide synthesis workflows and intermediate isolation requirements. The L-stereochemistry and difluoro aromatic substitution pattern provide a consistent, specification-driven input for manufacturing peptide intermediates used in research and development pipelines. The compound's structure enables conversion into sequence-defined fluorinated fragments that can be carried into further synthetic steps, supporting controlled manufacturing of specialty peptide materials and related fine chemicals.
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