Fmoc-2,3-Difluoro-L-Phenylalanine is an Fmoc-protected, fluorinated amino acid derivative in which the phenylalanine side chain is retained while fluorine atoms are introduced at the 2- and 3-positions of the amino acid backbone. The molecule contains an Fmoc carbamate on the amino group and a free carboxylic acid, and the difluoro substitution modifies the alpha-carbon environment and side-chain electronics while maintaining the L-configuration indicated in the name. It is used as a building block for stepwise peptide synthesis and structure-activity or labeling studies where fluorinated analogues provide altered sterics and hydrogen-bonding patterns compared with unmodified phenylalanine.
CAT No: CP12606
Fmoc-2,3-Difluoro-L-Phenylalanine is an Fmoc-protected L-phenylalanine derivative in which the α-carbon region bears two fluorine atoms at the 2,3-positions relative to the amino acid backbone. The molecule contains the stereodefined L-configuration at the chiral center, an aromatic side chain, and an N-(9H-fluoren-9-ylmethoxycarbonyl) protecting group that is compatible with standard base-mediated Fmoc deprotection. Two closely spaced C-F bonds introduce strong inductive effects and distinct metabolic and conformational behavior compared with non-fluorinated analogs, while the carbonyl and activated carboxyl functionality support peptide coupling chemistry after appropriate activation. The resulting fluorinated, N-protected amino acid intermediate is suited for incorporation into peptide building blocks and for downstream synthetic transformations that exploit the fluorinated backbone as a stereoelectronic handle in structure-guided design.
1. Peptide Synthesis
Fmoc-2,3-Difluoro-L-Phenylalanine is applied in peptide building block preparation for solid-phase and solution-phase peptide synthesis. The Fmoc group enables controlled N-terminal protection during chain assembly, while the difluorinated α,β-carbon framework and the L-stereocenter provide a defined fluorinated residue for peptide coupling chemistry. The carboxylate functionality can be activated under peptide coupling conditions to form amide bonds, allowing incorporation of this residue into peptide sequences where fluorine-driven conformational bias or altered physicochemical properties are desired. The fluorinated backbone can be retained through synthesis and used to generate peptide analog libraries for subsequent biochemical characterization and method development in amino acid chemistry.
2. Peptidomimetics And SAR
Fmoc-2,3-Difluoro-L-Phenylalanine supports peptidomimetic construction and structure-activity relationship studies by introducing a fluorinated phenylalanine motif with a stereodefined chiral center. The aromatic side chain and the difluoro-substituted backbone together create a rigidified electronic environment that can modulate hydrogen bonding patterns, dipole distribution, and local sterics within peptide-like scaffolds. Fmoc protection allows systematic substitution at the residue level, enabling parallel synthesis of analog series where the 2,3-difluoro motif is varied by position or neighboring residues. The resulting fluorinated peptide analogs serve as research intermediates for SAR workflows and molecular design efforts that rely on consistent stereochemistry and reproducible side-chain presentation.
3. Chemical Biology Labeling
Fmoc-2,3-Difluoro-L-Phenylalanine is utilized in chemical biology research where fluorinated amino acid residues act as chemically stable reporters or recognition elements within biomolecule constructs. The Fmoc-protected amine supports incorporation into peptides and peptide conjugates, while the difluorinated backbone can function as a distinct structural signature for analytical differentiation from non-fluorinated controls. The aromatic side chain can be leveraged for subsequent derivatization strategies on the peptide scaffold, including orthogonal functional group introduction at other positions while preserving the fluorinated residue. Downstream conjugate formation can employ the assembled peptide framework to generate biomolecule-modified probes, enabling studies that require defined stereochemistry and chemically robust C-F bonds.
4. Chiral Building Block Development
Fmoc-2,3-Difluoro-L-Phenylalanine is suitable as a chiral amino acid intermediate for stereoselective synthesis and method development in fluorinated building block chemistry. The L-configuration at the α-carbon provides a fixed stereochemical outcome for incorporation into larger frameworks, and the adjacent difluoro substitution provides a strong electronic differentiation that can influence subsequent functional group transformations. Fmoc protection offers a standardized handle for N-deprotection and re-protection workflows, supporting iterative synthesis of protected amino acid derivatives and peptide coupling-ready intermediates. The compound can also serve as a reference chiral component in synthetic organic chemistry where fluorinated stereocenters are required for reproducible downstream scaffold assembly.
5. Pharmaceutical Intermediate Preparation
Fmoc-2,3-Difluoro-L-Phenylalanine is relevant to pharmaceutical intermediate preparation in the context of fluorinated amino acid and peptide-manufacturing supply chains. The Fmoc-protected amino acid format aligns with established protected amino acid synthesis workflows, where controlled deprotection and coupling steps are used to assemble defined sequences or fragments for further processing. The difluorinated backbone can be carried through intermediate stages to produce fluorinated peptide segments, which may later be converted into larger drug-like molecules or used as building blocks for medicinal chemistry programs. Industrially, the compound's stable C-F bonds and protected amine/carboxyl functionality enable route design that emphasizes predictable handling of stereodefined intermediates for fine chemical synthesis.
6. Process Chemistry Intermediate
Fmoc-2,3-Difluoro-L-Phenylalanine is applied in process chemistry intermediate preparation where robust protecting-group logic and peptide-compatible functionality are required. The Fmoc group provides a clear protection/deprotection switch, supporting manufacturing-style sequences that separate N-protection control from coupling operations. The difluorinated α,β-carbon motif can be exploited to generate fluorinated intermediates that maintain structural integrity through multiple synthetic steps, including conversion to activated carboxyl derivatives for amide formation. The resulting fluorinated residue can be used to produce peptide fragments and peptidomimetic intermediates at scale, linking amino acid derivatization chemistry with industrial fine chemical production and downstream scaffold generation.
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