Cbz-2,4-Difluoro-L-Phenylalanine is a Cbz-protected, fluorinated amino acid derivative in which the phenylalanine side chain bears two fluorine substituents at the 2- and 4-positions of the aromatic ring. The molecule contains an amino functional group and a carboxyl group, with the amino functionality protected as a benzyloxycarbonyl (Cbz) carbamate, and it is specified as the L stereochemical form. In peptide chemistry and chemical biology workflows, this protected difluorophenylalanine analogue is used as a building block to introduce aryl fluorination into peptides or peptide-related intermediates while providing chemoselectivity during stepwise assembly and serving as a handle for structure-activity studies and analytical method development.
CAT No: CP12708
Cbz-2,4-Difluoro-L-Phenylalanine is an L-phenylalanine derivative bearing a benzyloxycarbonyl (Cbz) protecting group on the amino functionality and two fluorine atoms substituted at the 2- and 4-positions of the aromatic ring. The stereogenic center at the α-carbon is retained in the L-configuration, providing a defined chiral amino acid framework for peptide coupling chemistry. The Cbz carbamate can be removed under hydrogenolysis or strong nucleophilic conditions, while the aryl fluorines impart distinctive electronic effects and can participate in downstream functionalization or serve as stable handles for structure-property studies. As a protected amino acid intermediate, it combines a protected amine, a carboxyl group suitable for activation, and aryl fluorination patterns that support derivatization, peptidomimetic design, and synthetic method development.
1. Peptide Synthesis
Cbz-2,4-Difluoro-L-Phenylalanine is used in peptide building workflows where a Cbz-protected amino acid provides controlled N-terminus chemistry during stepwise coupling. The L-configuration at the α-carbon and the protected carbamate enable stereochemically consistent peptide bond formation after carboxyl activation, while the aromatic 2,4-difluoro substitution can tune hydrophobicity, conformational preferences, and aromatic electronics in the resulting peptide sequence. Cbz protection supports orthogonal deprotection strategies, allowing selective unmasking of the amine for subsequent elongation or fragment coupling. Downstream, the fluorinated phenylalanine residue can be incorporated into peptide analogs for scaffold optimization, linker studies, and mechanistic investigations that require defined aryl substitution patterns.
2. Peptidomimetics And SAR
Cbz-2,4-Difluoro-L-Phenylalanine is applied in peptidomimetic and SAR-focused medicinal chemistry campaigns that require fluorinated aromatic side chains to modulate binding interactions. The two ring fluorines at the 2- and 4-positions act as electron-withdrawing substituents and can influence hydrogen-bonding patterns, dipole moments, and metabolic stability trends in aromatic-containing analogs. The Cbz-protected amino acid form supports incorporation into constrained peptide-like structures through standard coupling chemistry, enabling systematic side-chain variation while maintaining a consistent stereochemical backbone. The resulting fluorinated residues can be used to generate structure-activity relationship libraries, support fragment-to-lead refinement, and provide chemically defined analogs for comparative binding and stability assessments.
3. Chemical Biology Conjugation
Cbz-2,4-Difluoro-L-Phenylalanine is suitable for chemical biology workflows that construct labeled or modified biomolecular probes through controlled peptide or protein fragment assembly. The protected amino acid framework enables incorporation of a fluorinated phenylalanine motif into peptides used as recognition elements, affinity handles, or substrates for downstream conjugation chemistries. Cbz deprotection can be leveraged to expose the amine for subsequent coupling to electrophiles or for generating reactive intermediates that attach tags, linkers, or capture moieties. The aryl fluorines provide stable, chemically robust features for probe characterization and for designing probes where aromatic electronics and sterics must be held constant across analog series.
4. Process Chemistry Intermediate
Cbz-2,4-Difluoro-L-Phenylalanine is employed as a chiral, protected amino acid intermediate in process chemistry intermediate preparation for fluorinated fine chemicals and peptide-manufacturing supply chains. The Cbz carbamate offers a practical protection strategy for the amino group during multi-step synthesis, while the L-configuration supports reproducible stereochemical outcomes in downstream couplings. The aromatic difluoro substitution supports predictable reactivity patterns during purification and subsequent functional transformations, and the protected amino acid format aligns with scalable activation and coupling approaches used in manufacturing settings. The compound can be used to prepare fluorinated peptide building blocks, peptidomimetic intermediates, and downstream derivatives that retain the 2,4-difluoro phenyl motif for consistent product specifications.
5. Analytical Reference Standards
Cbz-2,4-Difluoro-L-Phenylalanine is utilized for analytical research and method development where chemically defined fluorinated amino acid standards are required. The combination of a protected amino group (Cbz carbamate) and the 2,4-difluoro aromatic pattern provides distinguishable mass and fragmentation behavior in LC-MS and GC-MS workflows, supporting identification and quantitation of peptide hydrolysates or synthetic intermediates. The L-stereochemical assignment can be relevant for chiral chromatographic method development and for confirming stereochemical integrity during protected amino acid synthesis and peptide assembly. The compound can serve as a reference for monitoring derivatization, deprotection progression, and impurity profiling in amino acid derivative and peptide building block production.
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