Cbz-4-Fluoro-L-Phenylalanine is a Cbz-protected, fluorinated amino acid derivative in which the phenylalanine side chain bears a 4-fluoro substituent, with the amino acid backbone retaining the L stereochemical designation. The molecule contains a Cbz (benzyloxycarbonyl) carbamate protecting the amino group alongside a free carboxylic acid, and the aromatic side chain provides a fluorinated, electronically modified hydrophobic functionality for incorporation into peptide frameworks. As a protected amino acid building block, it is used in peptide synthesis workflows such as stepwise or solid-phase assembly to introduce the 4-fluoro-phenylalanine residue while maintaining chemoselective control over the protected amine during coupling and subsequent deprotection steps.
CAT No: CP14608
Cbz-4-Fluoro-L-Phenylalanine is a Cbz-protected L-phenylalanine derivative bearing a para-fluoro substituent on the aromatic side chain, providing a chiral amino acid framework with an N-Cbz carbamate and a free carboxylic acid. The para-fluorinated phenyl ring introduces distinctive electronic effects and a handle for downstream aryl functionalization, while the Cbz group supports orthogonal protection behavior during peptide coupling and selective deprotection. The compound's stereogenic center at the alpha carbon preserves L-configuration for stereochemically defined peptide incorporation, and the carboxylic acid enables conversion to activated esters or peptide coupling partners under standard amino acid chemistry. The combination of protected amine, acid functionality, and aryl fluorine makes it a practical intermediate for peptide building block preparation, aromatic substitution strategies, and structure-defined synthetic targets in both research and manufacturing settings.
1. Peptide Synthesis
Cbz-4-Fluoro-L-Phenylalanine supports peptide building block preparation in automated and manual peptide synthesis workflows by combining an N-Cbz carbamate with a carboxylic acid suitable for amide bond formation. The L-stereocenter enables stereochemically consistent incorporation into peptide chains, while the para-fluoro aromatic side chain can be retained through coupling and used as a defined substituent for later derivatization or SAR mapping. Cbz protection can be removed under conditions compatible with many peptide-resin and solution-phase strategies, enabling sequential N-terminal deprotection and iterative chain elongation. The resulting fluorinated peptide fragments and analogs can be used to generate structure-defined libraries and to probe how aryl electronics influence peptide conformation and binding interactions.
2. Side-Chain Functionalization
Cbz-4-Fluoro-L-Phenylalanine serves as a chemically targeted amino acid intermediate for side-chain functionalization where the para-fluorine on the phenyl ring acts as a reactive substituent for further synthetic elaboration. The aryl C-F bond can be leveraged in nucleophilic aromatic substitution or cross-coupling-compatible transformations to install additional substituents while maintaining the amino acid backbone integrity. The N-Cbz carbamate and carboxylic acid provide orthogonal functional groups for staged protection, activation, and coupling, allowing the fluorinated residue to be carried through multi-step sequences without losing the stereochemical definition at the alpha carbon. Downstream products include substituted aryl phenylalanine analogs, fluorine-retaining peptide intermediates, and derivatized aromatic fragments used in synthetic methodology development and fine chemical synthesis.
3. Drug Discovery SAR Studies
Cbz-4-Fluoro-L-Phenylalanine is applicable to medicinal chemistry research focused on structure-activity relationship studies of peptide-like scaffolds and peptidomimetics where defined aromatic substitution patterns are required. The para-fluoro phenyl group provides a distinct electronic and steric signature relative to unsubstituted phenylalanine, and the L-configuration ensures consistent stereochemical presentation within peptide analogs. Cbz protection allows controlled handling during synthesis of analog series, while the carboxylic acid functionality enables incorporation into amide-linked structures for systematic SAR comparisons. Fluorinated analogs generated from this intermediate can support fragment-based optimization, binding-site probing, and rational scaffold refinement using amino acid-derived substitution patterns.
4. Protected Amino Acid Chemistry
Cbz-4-Fluoro-L-Phenylalanine functions as a protected amino acid derivative for orthogonal protection and deprotection planning in multi-functional synthesis routes. The N-Cbz carbamate provides a stable amine protection strategy that can be maintained during activation of the carboxylic acid and subsequent coupling steps, while the free acid supports conversion to activated derivatives for peptide bond formation. The presence of the chiral alpha carbon and the para-fluoro aromatic substituent enables stereocontrolled preparation of chiral intermediates and downstream peptide building blocks with a defined substitution pattern. The compound can be employed as a controlled intermediate in process chemistry intermediate preparation where reproducible protection-state management is required for scalable fine chemical synthesis.
5. Pharmaceutical Manufacturing Intermediates
Cbz-4-Fluoro-L-Phenylalanine can be used in pharmaceutical manufacturing-oriented workflows as a defined fluorinated amino acid intermediate for producing peptide-based active pharmaceutical ingredient candidates and related process intermediates. The Cbz-protected amine and carboxylic acid combination supports standard peptide coupling chemistry and enables consistent incorporation of a fluorinated phenylalanine residue into larger intermediates under manufacturing-compatible synthetic sequences. The para-fluoro aromatic group can be carried through early stages to maintain structural fidelity, supporting downstream conversion into final fluorinated peptide or peptidomimetic intermediates. The compound's chiral, protection-state-defined nature makes it suitable for route design that emphasizes controlled functional group interconversions and reliable intermediate generation in applied chemical manufacturing.
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