Cbz-2,5-Difluoro-D-Phenylalanine is a protected, non-proteinogenic amino acid derivative featuring a benzyl side chain bearing two fluorine substituents at the 2- and 5-positions and a D-stereochemical configuration at the alpha carbon. The molecule contains a free carboxyl group and an amino group masked as a Cbz (benzyloxycarbonyl) carbamate, with the aromatic ring fluorination imparting distinctive electron-withdrawing character and altered physicochemical behavior relative to unsubstituted phenylalanine. In peptide chemistry, the Cbz-protected amino functionality supports chemoselective coupling steps while the difluoro-substituted aromatic side chain provides a handle for structure-activity studies, conformational or interaction mapping, and incorporation into synthetic peptide analogues for chemical biology investigations.
CAT No: CP12809
Cbz-2,5-Difluoro-D-Phenylalanine is a D-configuration phenylalanine derivative bearing two fluorine substituents at the 2- and 5-positions of the aromatic ring, combined with a benzyloxycarbonyl (Cbz) N-protecting group on the amino functionality. The molecule presents a chiral α-carbon suitable for stereochemically controlled peptide coupling, while the carboxyl group can be managed as a protected or reactive handle depending on the salt/activation state used in synthesis. Aromatic fluorination modulates electronics and can influence conformational preferences and binding-site interactions in peptide and peptidomimetic scaffolds, whereas the Cbz carbamate supports orthogonal protection strategies compatible with standard amino acid chemistry. The overall structure functions as a chiral amino acid intermediate that can undergo amide bond formation after activation and can be further elaborated through downstream transformations of the fluorinated aromatic side chain.
1. Peptide Synthesis
Cbz-2,5-Difluoro-D-Phenylalanine is applied in peptide building workflows where a D-amino acid residue with an N-Cbz carbamate is required for controlled incorporation into linear peptides and protected peptide fragments. The Cbz-protected amine participates in standard peptide coupling after carboxyl activation, while the stereogenic α-carbon enables retention of D-configuration during amide bond formation. Aromatic 2,5-difluorination provides a fluorinated side chain that can tune hydrophobicity, aromatic electronics, and local conformational behavior of the resulting peptide. The resulting fluorinated peptide products can serve as research materials for mapping side-chain recognition and for constructing peptide analogs with altered physicochemical profiles.
2. Peptidomimetics And SAR
Cbz-2,5-Difluoro-D-Phenylalanine supports medicinal chemistry programs focused on structure-activity relationship studies and peptidomimetic design, where fluorinated aromatic residues are used to probe binding interactions. The D-configuration and the fluorinated phenyl ring can be leveraged to modulate steric and electronic effects without changing the overall amino acid topology. Cbz protection enables sequential synthetic assembly, allowing selective deprotection and coupling steps to generate analog series with consistent stereochemical identity. Downstream derivatives can be converted into constrained scaffolds, fragment-linked constructs, or metabolically stable peptide mimics for SAR mapping and iterative molecular design.
3. Side-Chain Functionalization
Cbz-2,5-Difluoro-D-Phenylalanine is suitable for side-chain functionalization strategies in synthetic organic chemistry and chemical biology research, where fluorinated aromatic handles are used to direct subsequent derivatization. The fluorinated aromatic ring can participate in electrophilic aromatic substitution, cross-coupling, or selective substitution patterns depending on the substitution pattern and protecting-group state, enabling generation of substituted aryl analogs while maintaining the amino acid backbone. The Cbz carbamate and α-amino stereocenter allow the compound to be carried through multi-step sequences before final coupling or deprotection. The resulting functionalized amino acid derivatives can be used to build labeled probes, affinity reagents, or chemically diversified libraries for downstream molecular recognition studies.
4. Protected Amino Acid Chemistry
Cbz-2,5-Difluoro-D-Phenylalanine is utilized as a protected amino acid derivative for orthogonal protection and controlled deprotection planning in peptide and intermediate synthesis. The Cbz group provides an N-protection handle that can be removed under conditions compatible with many carboxyl-activation and side-chain manipulation workflows, supporting stepwise assembly of protected amino acid sequences. The presence of two aromatic fluorines improves chemical definition of the side chain and can reduce ambiguity in analytical characterization during intermediate purification and verification. The compound can therefore serve as a chiral building block for preparing peptide building blocks, activated fragments, and downstream chiral intermediates used in fine chemical synthesis.
5. Analytical Standards and Characterization
Cbz-2,5-Difluoro-D-Phenylalanine is applied in analytical research as a structurally defined chiral reference material for method development and characterization of fluorinated peptide intermediates. The combination of D-stereochemistry, Cbz carbamate, and the 2,5-difluorinated aromatic side chain creates a distinct mass and fragmentation signature that can support LC-MS, GC-MS, and NMR-based identification workflows. The compound's protected amine state enables consistent handling during analytical method screening and can be used to validate derivatization or coupling-related sample preparation steps. The resulting analytical utility extends to quality control of fluorinated amino acid incorporation in peptide synthesis and to verification of stereochemical integrity in chiral intermediate series.
6. Pharmaceutical Intermediate Preparation
Cbz-2,5-Difluoro-D-Phenylalanine is relevant to pharmaceutical intermediate preparation and process chemistry for generating fluorinated amino acid residues used in peptide-like drug candidates and advanced chemical entities. The chiral α-amino acid framework and N-Cbz protection facilitate scalable intermediate routing, where controlled deprotection and subsequent amide formation can be integrated into manufacturing sequences for protected peptide fragments. Aromatic fluorination supports downstream property tuning in drug-like scaffolds, and the defined substitution pattern can reduce variability when preparing analog series. The compound can be employed as a manufacturing-ready chiral building block for producing fluorinated intermediates that feed into larger synthetic routes for fine chemical production.
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