Cbz-3-Fluoro-L-Phenylalanine is a Cbz-protected, fluorinated amino acid derivative in which the phenylalanine scaffold bears a fluorine substituent at the 3-position of the aromatic ring and retains an L stereochemical configuration. The molecule contains an N-terminal benzyloxycarbonyl (Cbz) protecting group on the amino functionality and an unprotected carboxylic acid, while the side chain features a substituted benzyl group with a ring fluorine that can modulate polarity, hydrogen-bonding patterns, and aromatic electronic properties. It is used as a building block for peptide synthesis and structure-activity or chemical biology studies where incorporation of a 3-fluoro-substituted phenylalanine residue supports preparation of fluorinated peptides and related analytical or labeling targets.
CAT No: CP14508
Cbz-3-Fluoro-L-Phenylalanine is an N-Cbz protected L-phenylalanine derivative bearing a fluorine substituent at the 3-position of the aromatic ring. The molecule combines a stereogenic α-carbon from the L-amino acid framework with a benzyl carbamate protecting group on the amino functionality, while the side chain retains an aryl fluoride that can influence electronics and participate in downstream functionalization. The Cbz group supports standard peptide-coupling workflows by masking the amine during assembly and enabling controlled deprotection under hydrogenolysis conditions. The aryl C-F bond and fluorinated aromatic ring provide a stable, chemically informative handle for chiral building block design, medicinal chemistry-style SAR exploration, and synthetic intermediate preparation for fluorinated analogs.
1. Peptide Synthesis
Cbz-3-Fluoro-L-Phenylalanine is used as a protected amino acid building block in peptide synthesis where the Cbz carbamate masks the α-amino group for coupling compatibility. The L-configuration at the α-carbon supports stereochemically defined incorporation into growing peptide chains, while the fluorinated phenyl side chain remains intact through typical amide-forming steps. The aryl fluoride can be retained for later diversification or can be carried through to generate fluorinated peptide analogs for structure-function studies. Downstream deprotection and coupling strategies can be applied to assemble sequences containing 3-fluorophenylalanine motifs for biochemical research and peptidomimetic scaffold construction.
2. Side-Chain Functionalization
Cbz-3-Fluoro-L-Phenylalanine is applicable to side-chain functionalization and fluorinated intermediate generation in synthetic organic chemistry. The 3-fluoro substituent on the phenyl ring provides a chemically addressable handle for electrophilic aromatic substitution patterns, cross-coupling-compatible aryl fluoride chemistry, or conversion into other aryl functionalities depending on the chosen synthetic route. The N-Cbz protection supports selective transformations on the aromatic ring and minimizes undesired amine reactivity during derivatization. Resulting fluorinated amino acid derivatives can be used to access labeled or modified scaffolds for SAR studies, fragment elaboration, and downstream synthesis of fluorinated drug-like molecules.
3. Chiral Building Block Development
Cbz-3-Fluoro-L-Phenylalanine is suitable as a chiral amino acid intermediate for stereodefined synthesis of fluorinated analogs. The L-amino acid stereocenter and the protected carbamate enable controlled handling during multi-step routes that require chemoselective transformations without racemization at the α-carbon. The fluorinated aromatic side chain contributes defined physicochemical character that can be propagated into larger molecules, including peptides, peptidomimetics, and small-molecule fragments. The compound can serve as a starting point for preparing enantiopure fluorinated building blocks used in method development and stereochemical library construction.
4. Chemical Biology Research
Cbz-3-Fluoro-L-Phenylalanine is used in chemical biology and protein engineering workflows to introduce fluorinated phenylalanine residues into peptide or protein-like constructs. The Cbz-protected amine supports controlled incorporation during solid-phase or solution-phase assembly, while the fluorinated aromatic ring can modulate local polarity and serve as a spectroscopically informative motif for analytical tracking. The stable aryl fluoride can be carried into conjugation-ready intermediates or used to generate fluorinated analogs that probe binding-site tolerance and conformational effects. Downstream products derived from this amino acid building block can support biochemical research intermediate preparation for molecular recognition studies and structure-activity relationship investigations.
5. Pharmaceutical Intermediate Preparation
Cbz-3-Fluoro-L-Phenylalanine is relevant to pharmaceutical intermediate preparation and fine chemical synthesis focused on fluorinated amino acid content. The protected amino acid format aligns with industrially practiced protected amino acid chemistry, where N-protection enables reliable coupling and purification during manufacturing-scale intermediate generation. The fluorinated phenyl side chain can be maintained for incorporation into active-pharmacophore analogs or transformed into alternative aryl substituents in later synthetic stages. The resulting fluorinated derivatives can function as key intermediates for producing fluorinated drug candidates, peptidomimetic leads, and processable building blocks used in applied product development.
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