Cbz-2,6-Difluoro-D-Phenylalanine is a Cbz-protected, non-natural D-phenylalanine derivative bearing two fluorine atoms at the 2,6-positions of the aromatic side chain. The molecule contains a Cbz carbamate protecting group on the amino functionality and a free carboxyl group, and its side chain features a difluorinated benzyl ring whose electron-withdrawing fluorine substituents modify hydrophobicity and aromatic character while maintaining the D stereochemical configuration at the alpha carbon. As a protected amino acid intermediate, it is used in peptide synthesis and structure-activity studies where incorporation of a difluorinated phenylalanine residue and controlled amide-bond formation are required, and it can also serve as a defined building block for analytical method development and chemical biology labeling strategies that depend on fluorinated aromatic motifs.
CAT No: CP12909
Cbz-2,6-Difluoro-D-Phenylalanine is a D-configured phenylalanine derivative bearing two fluorine atoms at the 2 and 6 positions of the aromatic ring, alongside a benzyloxycarbonyl (Cbz) protecting group on the amino functionality. The molecule combines a chiral α-carbon with an aromatic side chain that is electronically modulated by ortho-difluoro substitution, which can influence conformational preferences and peptide-side-chain recognition during coupling and subsequent transformations. The Cbz group provides an acid-stable N-protection handle that can be removed under hydrogenolysis-compatible conditions, while the fluorinated aryl system can participate in halogen-mediated interactions and serves as a robust motif for downstream derivatization. As a chiral amino acid intermediate, Cbz-2,6-Difluoro-D-Phenylalanine supports peptide building block preparation and stereochemically defined incorporation into fluorinated peptide analogs and structure-focused chemical libraries.
1. Peptide Synthesis
Cbz-2,6-Difluoro-D-Phenylalanine is applied in peptide synthesis workflows where a protected, stereodefined amino acid building block is required for controlled amide bond formation. The Cbz-protected amine and the free carboxyl functionality enable standard peptide coupling strategies while maintaining D-configuration at the α-carbon, supporting stereochemically consistent peptide assembly. The ortho-difluorophenyl side chain can be incorporated as a conformationally and electronically tuned residue, which may affect local backbone dynamics and aromatic packing in peptide sequences. Fluorinated peptide products generated from this intermediate can be used to probe sequence-dependent behavior and to prepare peptidomimetic scaffolds with defined aromatic substitution patterns for downstream medicinal chemistry and materials-oriented research.
2. Peptidomimetics And SAR Studies
Cbz-2,6-Difluoro-D-Phenylalanine is suited for peptidomimetic construction and structure-activity relationship studies that require systematic variation of aromatic electronics and steric profile. The 2,6-difluoro substitution pattern on the phenyl ring can modulate hydrogen-bonding patterns, dipole distribution, and aromatic interaction strength, while the D-amino acid stereochemistry provides a handle for mapping stereochemical effects in analog series. The Cbz-protected nitrogen supports iterative synthesis of analogs where side-chain electronics remain constant across a library, enabling meaningful comparison of structure-dependent properties. Fluorinated peptide analogs and constrained peptidomimetics derived from this building block can serve as research intermediates for SAR mapping, fragment-to-lead optimization, and receptor-binding motif studies in chemical biology programs.
3. Chemical Biology Labeling
Cbz-2,6-Difluoro-D-Phenylalanine is used in chemical biology research settings to introduce fluorinated aromatic residues into probe molecules and biomolecule-interacting constructs. The protected amino acid form supports incorporation into peptides, enabling subsequent deprotection and functionalization steps that can be aligned with conjugation strategies such as linker attachment or orthogonal handle installation on the peptide scaffold. The fluorinated phenyl side chain can function as a stable, spectroscopically informative motif for analytical tracking, and its halogen pattern may support specific molecular recognition through halogen-bonding interactions. Derivatives prepared from this intermediate can be applied as labeling components, affinity probes, or scaffold elements in studies that require defined stereochemistry and controlled aromatic substitution for reproducible molecular behavior.
4. Protected Amino Acid Chemistry
Cbz-2,6-Difluoro-D-Phenylalanine is employed as a protected amino acid derivative in synthetic methodology development and intermediate preparation for multi-step chiral synthesis. The Cbz group provides a chemically distinct N-protection strategy that can be carried through coupling and intermediate transformations, while maintaining a protected amine suitable for sequential synthetic operations. The D-configuration and the electron-poor, sterically hindered 2,6-difluorophenyl ring can influence reactivity during downstream functional group manipulations, supporting route design for fluorinated amino acid derivatives. Conversion of this intermediate into additional protected or functionalized forms enables access to C-terminal or side-chain-modified analogs, supporting fine chemical synthesis and chiral building block supply for peptide-focused manufacturing and research pipelines.
5. Pharmaceutical Intermediate Preparation
Cbz-2,6-Difluoro-D-Phenylalanine is relevant to pharmaceutical intermediate preparation where fluorinated amino acid motifs are incorporated into drug-like peptidic or peptidomimetic candidates. The protected amino acid format supports scalable peptide coupling chemistry and enables manufacturing-friendly intermediate handling prior to final deprotection and assembly steps. The fluorinated aromatic side chain can be leveraged to tune physicochemical properties such as metabolic stability and binding-site complementarity in fluorinated analog series, while the D-stereocenter provides a defined stereochemical element for synthetic control. Downstream derivatives formed from this intermediate can feed into process chemistry for producing fluorinated peptide fragments, standardized building blocks for combinatorial synthesis, and defined intermediates used in specialty chemical production.
6. Analytical Research Standards
Cbz-2,6-Difluoro-D-Phenylalanine is used to generate analytical standards and reference materials for method development involving fluorinated amino acids and peptide analogs. The combination of Cbz-protected nitrogen and a D-configured, ortho-difluorinated phenyl side chain provides a structurally distinctive target that can support unambiguous identification in chromatographic and spectrometric workflows. Fluorinated peptide derivatives prepared from this building block can serve as calibration compounds or retention-time anchors when developing assays for peptide synthesis monitoring, impurity profiling, or stability studies of fluorinated peptidic products. The stereochemical integrity and defined aromatic substitution pattern make this intermediate suitable for producing consistent analytical benchmarks that support applied research and quality-oriented synthetic development.
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