Cbz-2,6-Difluoro-L-Phenylalanine is a Cbz-protected, L-configured phenylalanine derivative in which two fluorine atoms are installed at the 2 and 6 positions of the aromatic side chain, modifying the steric and electronic character of the benzyl-like group. The molecule contains a free carboxyl group and an N-Cbz protecting group on the amino functionality, while the difluorinated phenyl ring provides increased fluorine substitution suitable for chemical labeling, spectroscopic differentiation, and altered hydrophobicity and conformational preferences in peptide contexts. In synthetic peptide chemistry and structure-activity studies, it functions as a protected amino acid building block for incorporating a difluorinated phenylalanine residue into peptides and for preparing fluorine-containing analogues used in analytical method development and molecular characterization.
CAT No: CP12908
Cbz-2,6-Difluoro-L-Phenylalanine is an L-phenylalanine derivative bearing a benzyloxycarbonyl (Cbz) protecting group on the amino functionality and two fluorine atoms at the 2- and 6-positions of the aromatic ring. The molecule retains the chiral alpha-carbon typical of amino acid building blocks, pairing an L-stereocenter with a carboxylic acid functionality suitable for amide formation after activation. The electron-withdrawing fluorines modulate aromatic reactivity and influence conformational preferences through steric and inductive effects, while the Cbz group enables controlled N-protection and hydrogenolysis-based deprotection. As a chiral amino acid intermediate, it can participate in peptide coupling chemistry and downstream aromatic functionalization strategies that leverage fluorinated aryl properties.
1. Peptide Synthesis
Cbz-2,6-Difluoro-L-Phenylalanine serves as an N-Cbz protected amino acid building block for peptide coupling workflows in research and fine chemical synthesis. The Cbz-protected amine supports standard peptide bond formation at the alpha-carboxyl group, while the L-configuration provides stereochemical fidelity in the resulting amide linkage. The 2,6-difluoro-substituted phenyl side chain can be incorporated into peptide sequences to introduce aryl fluorination patterns that may affect local hydrophobicity, packing, and metabolic stability relevant to peptide analog design. The Cbz group can be removed under hydrogenolysis-compatible conditions to enable iterative chain assembly and subsequent derivatization of the newly exposed amine. Incorporation into peptide fragments and longer constructs supports structure-driven studies of fluorinated side-chain effects in amino acid chemistry and peptide science.
2. Side-Chain Functionalization
Cbz-2,6-Difluoro-L-Phenylalanine enables side-chain functionalization strategies where fluorinated aromatic handles can be retained or transformed for downstream synthetic elaboration. The two fluorine substituents at the 2,6-positions create a defined electronic environment on the phenyl ring, which can influence subsequent electrophilic aromatic substitution patterns or nucleophilic aromatic substitution routes after appropriate activation. The amino acid backbone, protected as Cbz, allows selective manipulation of the side-chain aryl without prematurely exposing the amine during intermediate handling. The resulting fluorinated aryl derivatives can be used to generate peptidomimetic scaffolds, diversify SAR libraries, or prepare substituted aromatic analogs for chemical biology probes. This makes the compound a practical chiral intermediate for constructing fluorinated aromatic motifs from an amino acid starting point.
3. Chemical Biology Probes
Cbz-2,6-Difluoro-L-Phenylalanine supports chemical biology research requiring fluorinated aromatic residues for probe design and molecular recognition studies. The Cbz-protected amine and carboxyl functionality allow incorporation into peptide-like ligands, where the L-configuration maintains stereochemical control of the backbone. The 2,6-difluoro phenyl side chain can function as a defined steric and electronic element that may modulate binding interactions in protein-ligand contexts without altering the core amino acid geometry. The protected amino acid format facilitates sequential synthesis of labeled or tagged biomolecule fragments, including constructs that can later undergo deprotection to enable conjugation. Downstream use can include generation of fluorinated peptide analogs for studying structure-function relationships and for producing defined chemical tools in biochemical research.
4. Protected Amino Acid Chemistry
Cbz-2,6-Difluoro-L-Phenylalanine is suitable for protected amino acid chemistry workflows that rely on orthogonal control of N-protection during peptide building block preparation. The Cbz group provides a removable N-protection strategy compatible with hydrogenolysis, supporting controlled exposure of the amino functionality for subsequent coupling steps or for terminal functionalization. The presence of a chiral alpha-carbon and a carboxylic acid group enables predictable conversion into activated coupling partners while preserving stereochemical integrity through intermediate handling. The difluorinated aromatic side chain adds a chemically informative element that can be carried through multi-step synthesis as a stable substituent pattern. As a chiral synthetic intermediate, it can be employed in process chemistry intermediate preparation where reproducible protection-deprotection sequences are required for manufacturing-grade peptide fragments and fluorinated amino acid derivatives.
5. Pharmaceutical Intermediate Preparation
Cbz-2,6-Difluoro-L-Phenylalanine can be applied in pharmaceutical intermediate preparation for fluorinated amino acid derivatives used in medicinal chemistry and peptidomimetic development. The amino acid architecture, featuring a protected amine and carboxylic acid functionality, supports conversion into peptide coupling-ready intermediates and facilitates incorporation into constrained or modified scaffolds. The 2,6-difluoro aromatic substitution pattern provides a handle for tuning physicochemical properties such as aromatic electronics and steric shielding, which is relevant when generating fluorinated analog series for SAR studies. Cbz protection supports manufacturing-compatible sequence design by allowing iterative assembly and controlled deprotection prior to downstream transformations. The compound therefore functions as a chiral, structurally defined intermediate that can feed into fine chemical synthesis of fluorinated peptide-like building blocks and related drug-discovery chemistry targets.
6. Analytical Research Standards
Cbz-2,6-Difluoro-L-Phenylalanine is suitable for analytical research as a structurally defined fluorinated amino acid reference material and process-monitoring intermediate. The combination of Cbz-protected amine, carboxylic acid functionality, and a stereochemically defined L-center provides a distinct chemical signature for chromatographic and spectrometric characterization of fluorinated amino acid derivatives. The 2,6-difluoro phenyl group can improve detectability and facilitate method development for monitoring incorporation or conversion of difluorinated aromatic residues during peptide synthesis. The compound can also serve as a calibration or identity standard when evaluating protected amino acid intermediates, deprotection outcomes, or side-chain integrity in synthetic sequences. Its defined structure supports robust analytical method transfer across amino acid derivative synthesis and peptide construction workflows.
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