Cbz-2,3-Difluoro-D-Phenylalanine is a Cbz-protected, non-natural amino acid derivative featuring a D-phenylalanine backbone bearing two fluorine atoms at the 2- and 3-positions of the side-chain aromatic carbon framework. The molecule contains an amino functionality masked as part of the Cbz carbamate and a carboxyl group present as the free amino acid functionality, while the difluorinated aromatic substitution modulates side-chain electronics and steric and hydrogen-bonding characteristics relative to unsubstituted phenylalanine. In peptide chemistry and chemical biology workflows, this protected analogue is used as a building block for incorporating a difluorinated phenylalanine residue in stepwise synthesis and for structure-activity, labeling, or conformational studies where fluorine substitution and controlled amine reactivity are required.
CAT No: CP12609
Cbz-2,3-Difluoro-D-Phenylalanine is a Cbz-protected D-phenylalanine derivative bearing two fluorine atoms at the 2- and 3-positions of the amino-acid backbone, creating a difluorinated chiral center environment that can strongly influence peptide conformations and amide bond formation kinetics. The molecule contains a carbobenzyloxy (Cbz) group on nitrogen, a free carboxylic acid (or carboxyl functionality depending on the supplied form), and a benzyl side chain that supports standard amino-acid coupling chemistry. The geminal/adjacent fluorination pattern increases carbon-fluorine bond stability while providing electron-withdrawing character that can modulate reactivity during activation, coupling, and downstream transformations. As a chiral, N-protected amino-acid building block, Cbz-2,3-Difluoro-D-Phenylalanine functions as a stereochemically defined intermediate for protected amino acid synthesis, peptide construction, and fluorinated analog generation.
1. Peptide Synthesis
Cbz-2,3-Difluoro-D-Phenylalanine is used in peptide synthesis workflows to introduce a D-configured, difluorinated phenylalanine residue into peptide chains for conformationally tuned analogs. The Cbz-protected amine supports orthogonal peptide coupling strategies, while the difluorinated backbone provides a fluorine-rich motif that can be carried through amide bond formation without requiring side-chain modification. Carboxyl activation followed by amide coupling can incorporate the residue into protected peptide intermediates, enabling stepwise assembly of peptide building block preparations and subsequent Cbz deprotection to expose the next coupling handle. Fluorinated peptide analogs prepared from this amino acid derivative can be used to probe how backbone electronics and stereochemistry affect structure, stability, and sequence-dependent behavior in peptide science and chemical biology.
2. Peptidomimetics And SAR
Cbz-2,3-Difluoro-D-Phenylalanine is applied in peptidomimetic construction and structure-activity relationship studies where fluorinated backbone residues help tune hydrogen-bonding patterns and local sterics. The D-configuration and 2,3-difluorination create a defined stereochemical and electronic signature that can be retained during peptide analog synthesis, supporting systematic SAR studies across series of fluorinated analogs. Cbz protection enables controlled N-deprotection and iterative incorporation into larger scaffolds, while the phenyl side chain allows direct comparison to phenylalanine-based reference sequences. Downstream derivatives prepared from this building block can serve as fluorinated molecular fragments for medicinal chemistry exploration, enabling structure-guided optimization of peptide-like ligands and constrained conformations.
3. Chemical Biology Probes
Cbz-2,3-Difluoro-D-Phenylalanine is suitable for chemical biology research where fluorinated amino-acid analogs function as probes for backbone recognition and molecular interaction mapping. The difluorinated backbone can participate in specific physicochemical effects, such as altered polarity and modified amide microenvironments, while the phenyl side chain preserves aromatic interaction potential commonly associated with phenylalanine motifs. Cbz protection supports integration into peptide or protein fragments under standard protected amino acid chemistry, allowing the labeled residue to be positioned at defined sequence locations. Resulting fluorinated biomolecular constructs can be employed in binding studies, interaction assays, and mechanistic investigations that rely on stereodefined amino-acid incorporation and stable carbon-fluorine functionality.
4. Analytical Standards and LC-NMR Method Development
Cbz-2,3-Difluoro-D-Phenylalanine is used as an analytical reference and method development standard for quantifying fluorinated amino-acid derivatives and monitoring peptide synthesis intermediates. The presence of two fluorine atoms and a Cbz-protected nitrogen provides distinctive spectroscopic signatures that can support targeted identification by 19F NMR and LC-MS workflows. Carboxyl functionality and the Cbz group enable reproducible handling within protected amino acid synthesis and allow comparison against downstream deprotected or coupled products. Analytical research applications include calibration of detection methods for fluorinated building blocks, impurity profiling during peptide assembly, and verification of stereochemical integrity in chiral amino-acid intermediate preparation.
5. Pharmaceutical Intermediate Preparation
Cbz-2,3-Difluoro-D-Phenylalanine is relevant to pharmaceutical manufacturing and fine chemical synthesis as a chiral, N-protected amino-acid intermediate for producing fluorinated peptide-like intermediates. The Cbz group supports established protection/deprotection logic in process chemistry, while the difluorinated backbone can be carried through coupling steps to generate stable fluorinated motifs used in medicinal chemistry programs. The D-stereochemistry provides a controlled stereochemical input for downstream fragment assembly, enabling consistent manufacturing route design for peptide analogs and peptidomimetic building blocks. Industrially, the compound can be incorporated into workflows that require robust chiral amino acid derivatives and predictable peptide coupling compatibility for scale-up of fluorinated intermediates.
6. Side-Chain And Backbone Functionalization
Cbz-2,3-Difluoro-D-Phenylalanine is applied in amino acid derivatization and synthetic organic chemistry where fluorinated backbone residues serve as handles for further molecular modification. The Cbz-protected amine allows selective deprotection to generate the next coupling site, while the difluorinated 2,3-backbone can influence subsequent transformations by stabilizing intermediates and modulating reactivity of adjacent functional groups. The phenylalanine side chain can be retained for aromatic conjugation strategies or used as a reference point in scaffold diversification, supporting the construction of fluorinated analog libraries. Downstream, derivatives derived from this chiral amino-acid intermediate can feed into combinatorial synthesis, fragment-based molecular design, and stereochemically defined peptide science programs that require precise control of backbone fluorination and N-protection state.
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