Cbz-2-Fluoro-L-Phenylalanine is a Cbz-protected, fluorinated amino acid derivative in which the phenylalanine side chain is retained and a fluorine substituent is present at the 2-position relative to the amino acid backbone. The molecule bears a carboxyl group that is protected as part of the amino acid derivative framework and an N-terminus protected by the benzyloxycarbonyl (Cbz) group, with L-stereochemistry specified for the amino acid center and a 2-fluoro substitution that alters polarity and steric/inductive effects on the alpha-carbon. In peptide and amino acid synthesis workflows, the Cbz protecting group supports chemoselective handling of the amino functionality while the fluorinated stereodefined residue provides a handle for structure-activity studies, analogue libraries, and incorporation into peptide-related intermediates for analytical or chemical biology experiments.
CAT No: CP14408
Cbz-2-Fluoro-L-Phenylalanine is an N-Cbz-protected L-phenylalanine analog bearing a stereogenic center at the α-position and a fluorine substituent at C2 adjacent to the amino acid backbone. The molecule contains a benzyloxycarbonyl (Cbz) carbamate that masks the amino functionality for controlled peptide coupling, while the carboxylic acid (or its protected acid form, depending on handling) provides a defined handle for activation and amide bond formation. The 2-fluoro substitution introduces strong inductive effects and a C-F bond that can modulate conformational preferences, metabolic stability proxies, and reactivity patterns during downstream derivatization. As a chiral amino acid intermediate, it is suitable for stereochemically consistent incorporation into peptide building blocks and for generating fluorinated analogs used in structure-focused synthetic and biochemical studies.
1. Peptide Synthesis
Cbz-2-Fluoro-L-Phenylalanine is used in peptide synthesis as a protected amino acid building block where the Cbz carbamate supports standard peptide coupling workflows while maintaining the L-configuration at the α-carbon. The α-fluorine substituent at the backbone position can influence coupling-adjacent stereoelectronics and can be retained through amide bond formation to generate 2-fluoro-containing peptide analogs. The carboxylic acid functionality enables activation to form peptide bonds, and the N-protection strategy supports orthogonal deprotection planning when assembling multi-residue sequences. Fluorinated peptides derived from this amino acid are commonly employed to probe backbone effects, guide analog libraries, and support synthetic methodology development in peptide science.
2. Chiral Building Block Development
Cbz-2-Fluoro-L-Phenylalanine serves as a chiral amino acid intermediate for stereoselective synthesis of fluorinated stereochemical motifs used in medicinal chemistry and chemical biology. The defined L-stereochemistry and the adjacent C2 fluorine provide a controlled stereoelectronic environment that can be carried into downstream transformations without scrambling the stereocenter. The Cbz protecting group enables stepwise functional group management, allowing selective conversion of the carboxyl group and later removal of the N-protecting group when required for further coupling or derivatization. Fluorinated phenylalanine analogs prepared from this intermediate can be applied to generate stereochemically defined fragments for peptidomimetics, SAR studies, and chiral scaffold diversification.
3. Side-Chain Functionalization
Cbz-2-Fluoro-L-Phenylalanine is applicable to side-chain and backbone functionalization strategies aimed at producing fluorinated amino acid derivatives and peptidomimetic precursors. The aromatic phenyl side chain provides a stable hydrophobic handle for conjugation, while the backbone C-F bond can enable targeted chemical modification strategies that preserve the α-fluoro stereocenter. The N-Cbz protection supports selective chemistry on the carboxyl group and can be integrated into protecting-group schemes that separate amine masking from subsequent transformations. Fluorinated derivatives generated from this intermediate can be used as biochemical research reagents, scaffold components for molecular design, and intermediates for constructing fluorine-enriched libraries in fine chemical synthesis.
4. Bioconjugation Chemistry
Cbz-2-Fluoro-L-Phenylalanine can be incorporated into bioconjugation workflows where fluorinated amino acid residues are introduced to tune labeling stability and analytical detectability. The protected amine and carboxyl functionality allow conversion into activated derivatives that can participate in amide-forming conjugation chemistry, while the Cbz group supports controlled handling during multistep synthesis. The presence of the α-fluorine can influence local polarity and can be leveraged to create fluorine-containing conjugates suitable for mass spectrometric tracking and structural verification. Fluorinated peptide or protein conjugates derived from this amino acid analog may serve as tools for chemical biology investigations, biomolecule labeling studies, and structure-resolved interaction mapping.
5. Pharmaceutical Intermediate Preparation
Cbz-2-Fluoro-L-Phenylalanine is suitable for pharmaceutical intermediate preparation in the context of fluorinated amino acid and peptide analog manufacturing routes. The N-Cbz carbamate provides a robust protection strategy that can withstand typical coupling and activation conditions used to build peptide-like intermediates in process chemistry. The α-fluorinated backbone can be carried through synthetic sequences to yield defined fluorinated residues for downstream assembly into larger drug-like structures or peptidomimetic candidates. The compound's chiral, protected amino acid character supports reproducible intermediate generation for specialty chemical production and industrial fine chemical synthesis where stereochemical integrity and functional group orthogonality are required.
6. Analytical Research Standards
Cbz-2-Fluoro-L-Phenylalanine is applicable as an analytical research reference material and method-development intermediate for characterizing fluorinated peptides and amino acid derivatives. The combination of Cbz-protected amine and the α-fluoro stereocenter produces a well-defined chemical signature that can support LC-MS and NMR-based identification of fluorinated residues in complex mixtures. The protected amino acid format also enables preparation of calibration standards or fragment standards that reflect the same protecting-group state used in peptide coupling and subsequent deprotection steps. Incorporation into analytical workflows supports structure verification, impurity profiling, and stereochemical consistency checks across fluorinated amino acid derivative synthesis.
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