Cbz-2,5-Difluoro-L-Phenylalanine is a protected, fluorinated phenylalanine derivative in which the α-amino group is carbobenzyloxy (Cbz) protected and the aromatic side chain bears two fluorine substituents at the 2- and 5-positions relative to the benzylic carbon. The molecule contains a free carboxylic acid functionality and a stereogenic center at the α-carbon specified as L, with the difluoro-substituted phenyl ring providing altered electronic and steric characteristics compared with unsubstituted phenylalanine. As a Cbz-protected amino acid, it is used as a building block for stepwise peptide synthesis and for structure-activity or chemical biology studies where aryl fluorination and side-chain electronic modulation are used to probe peptide conformation, binding interactions, or labeling behavior.
CAT No: CP12808
Cbz-2,5-Difluoro-L-Phenylalanine is an L-phenylalanine derivative bearing two fluorine substituents at the 2- and 5-positions of the aromatic ring and a benzyloxycarbonyl (Cbz) group on the amino functionality. The molecule retains the stereogenic α-carbon of the L-amino acid, providing a defined chiral center for asymmetric peptide coupling and stereochemical fidelity during synthesis. The Cbz-protected amine and the carboxylic acid (or acid-equivalent form depending on the supplier grade) create a protected amino acid platform compatible with standard peptide coupling chemistries, while the aryl fluorines introduce strong inductive effects and enable regio-defined aromatic functional transformations. The combination of protected functionality and fluorinated side-chain electronics makes Cbz-2,5-Difluoro-L-Phenylalanine a practical chiral building block for preparing fluorinated peptide analogs, SAR-focused fragments, and downstream synthetic intermediates in fine chemical and biochemical research.
1. Peptide Synthesis
Cbz-2,5-Difluoro-L-Phenylalanine supports peptide building-block workflows in solid-phase and solution-phase synthesis by combining a Cbz-protected amine with an amino acid backbone suitable for amide bond formation at the α-carboxyl group. The L-configuration at the stereogenic center helps maintain stereochemical integrity when incorporated as a residue into peptide chains, while the 2,5-difluorophenyl side chain can tune aromatic interactions and metabolic stability in peptidomimetic designs. Cbz protection enables controlled deprotection steps that can be synchronized with coupling cycles, and the fluorinated aromatic ring can withstand many peptide-manufacturing conditions without losing structural definition. Fluorinated peptide analogs prepared from this residue can serve as reference standards, SAR probes, and mechanistic tools for studying sequence-dependent recognition.
2. Side-Chain Functionalization
Cbz-2,5-Difluoro-L-Phenylalanine enables side-chain derivatization strategies that exploit the distinct reactivity of fluorinated aromatic rings for subsequent synthetic diversification. The 2,5-difluoro substitution pattern can participate in nucleophilic aromatic substitution, cross-coupling, or selective functional group installation routes after peptide assembly or at the protected amino acid stage, allowing conversion of the aryl fluorines into alternative substituents while preserving the chiral amino acid core. The Cbz group provides orthogonal protection that can be removed or retained depending on whether the transformation targets the aromatic ring or the peptide coupling handle. Downstream products can include fluorine-to-heteroatom substituted analogs, aryl-expanded fragments, and labeled or scaffold-modified intermediates that feed into medicinal chemistry and chemical biology programs.
3. Chiral Amino Acid Intermediate
Cbz-2,5-Difluoro-L-Phenylalanine functions as a chiral amino acid intermediate for stereocontrolled synthesis of fluorinated building blocks used in fragment-based molecular design and peptidomimetic construction. The defined L-α-configuration and the Cbz-protected amine provide a stable platform for protecting-group management, enabling sequential transformations where the amino functionality remains masked during aromatic or side-chain modifications. The carboxyl functionality supports conversion into activated derivatives for coupling, while the aryl fluorines provide electronic differentiation that can be carried through to final intermediates for SAR studies. The resulting fluorinated chiral products can be used to generate libraries of amino acid derivatives, peptide-like scaffolds, and process-ready intermediates for fine chemical manufacturing.
4. Chemical Biology And Protein Engineering
Cbz-2,5-Difluoro-L-Phenylalanine can be applied in chemical biology and protein engineering contexts where fluorinated aromatic residues are used to modulate molecular recognition and to create chemically defined probes. The Cbz-protected amino acid format supports incorporation into peptide constructs that may be used as enzyme substrates, binding antagonists, or structural mimics in biochemical assays, with the 2,5-difluorophenyl group providing a tunable aryl environment for interaction studies. The stereogenic L-center ensures that the residue geometry aligns with peptide backbone conformations, supporting meaningful comparisons across analog series. Fluorinated peptide or protein fragment analogs derived from this building block can also serve as reference materials for affinity studies, structural mapping, and interaction characterization in applied biochemical research.
5. Pharmaceutical Manufacturing Intermediate
Cbz-2,5-Difluoro-L-Phenylalanine is suitable for pharmaceutical manufacturing intermediate preparation in routes that require fluorinated amino acid residues for peptide drug substance or peptide-like intermediate construction. The Cbz protecting group supports robust, scalable protection-deprotection logic that can be integrated into controlled manufacturing sequences, while the difluorinated phenyl side chain can be carried into higher-order intermediates without losing the regiochemical fluorine pattern. The amino acid scaffold enables conversion into coupling-ready forms for incorporation into longer sequences, and the fluorinated aromatic ring can contribute to downstream analytical detectability and impurity profiling due to its distinct chemical signature. Industrially, this residue can be employed to manufacture fluorinated peptide intermediates, building-block mixtures for process development, and chemically characterized materials used in downstream synthetic and analytical workflows.
6. Analytical Research Standards
Cbz-2,5-Difluoro-L-Phenylalanine can serve as an analytical research standard and reference intermediate for method development targeting fluorinated amino acid derivatives and peptide analogs. The combination of Cbz protection and a 2,5-difluorophenyl side chain creates a chemically distinctive signature that can improve chromatographic separation and mass spectrometric identification of related compounds in complex matrices. The defined stereochemistry and protected functional groups help generate reproducible reference materials for calibrations, impurity tracking, and structural verification during peptide synthesis and derivatization studies. Analytical workflows can leverage this compound to support characterization of fluorinated peptide building blocks, side-chain modified analogs, and process intermediates encountered in fine chemical synthesis.
If you have any peptide synthesis requirement in mind, please do not hesitate to contact us at . We will endeavor to provide highly satisfying products and services.
Creative Peptides is a trusted CDMO partner specializing in high-quality peptide synthesis, conjugation, and manufacturing under strict cGMP compliance. With advanced technology platforms and a team of experienced scientists, we deliver tailored peptide solutions to support drug discovery, clinical development, and cosmetic innovation worldwide.
From custom peptide synthesis to complex peptide-drug conjugates, we provide flexible, end-to-end services designed to accelerate timelines and ensure regulatory excellence. Our commitment to quality, reliability, and innovation has made us a preferred partner across the pharmaceutical, biotechnology, and personal care industries.
Read More