Cbz-2,4,6-Trifluoro-D-Phenylalanine is a Cbz-protected, non-natural amino acid derivative featuring a D-phenylalanine backbone bearing three fluorine substituents at the 2, 4, and 6 positions of the aromatic ring. The molecule contains a carboxyl group masked as a free acid (as implied by the amino acid derivative naming) and an N-terminus protected by a benzyloxycarbonyl (Cbz) carbamate, while the fluorinated phenyl side chain provides increased electron-withdrawing character and altered hydrophobicity compared with unsubstituted phenylalanine. In peptide chemistry and chemical biology workflows, this protected fluorinated amino acid is used as a building block to introduce aryl fluorination patterns into peptides or peptide-related intermediates for structure-activity studies, conformational or labeling investigations, and analytical method development targeting fluorinated aromatic motifs.
CAT No: CP17009
Cbz-2,4,6-Trifluoro-D-Phenylalanine is a Cbz-protected D-phenylalanine derivative bearing a trisubstituted aromatic ring with fluorine atoms at the 2, 4, and 6 positions. The molecule combines a benzyloxycarbonyl (Cbz) carbamate at the amino terminus with a stereogenic center at the alpha carbon, enabling stereochemically controlled incorporation into peptide-like architectures. The electron-withdrawing fluorinated phenyl ring modulates aromatic reactivity, amide formation behavior, and downstream derivatization options while maintaining a rigid, hydrophobic side chain for molecular recognition studies. As a chiral, protected amino acid intermediate, it can participate in standard peptide coupling chemistries after appropriate deprotection or activation strategies, and it can serve as a fluorinated aromatic motif for synthetic and analytical workflows.
1. Peptide Synthesis
Cbz-2,4,6-Trifluoro-D-Phenylalanine is used in peptide building workflows where a protected D-amino acid residue is required for stereodefined chain assembly. The Cbz carbamate protects the amino functionality during coupling, while the alpha-carboxyl group can be activated to form amide bonds with activated carboxylic acid partners. The D-configuration supports incorporation of non-L stereochemistry to probe conformational effects, protease selectivity, and backbone recognition in peptide analogs. The fluorinated aromatic side chain provides a chemically stable handle for constructing fluorinated peptides and peptidomimetics that can be carried through iterative synthesis and purification steps.
2. Peptidomimetics And SAR Studies
Cbz-2,4,6-Trifluoro-D-Phenylalanine is applied in medicinal chemistry-oriented structure-activity relationship studies that require a defined fluorinated aromatic substituent. The 2,4,6-trifluoro substitution pattern increases aromatic electron deficiency and can influence hydrogen-bonding patterns, lipophilicity, and conformational preferences of peptide-like scaffolds. The protected D-amino acid format enables controlled placement into peptidomimetic sequences, supporting systematic comparison of stereochemistry and side-chain electronics across analog series. The resulting fluorinated derivatives can be used as reference scaffolds for SAR mapping and for generating chemically consistent libraries of amino acid-modified compounds.
3. Chemical Biology Labeling
Cbz-2,4,6-Trifluoro-D-Phenylalanine can serve as a fluorinated amino acid component for chemical biology experiments that rely on stable aromatic motifs for tracking and detection. The Cbz-protected amino group supports stepwise synthesis of labeled or tagged peptides, while the fluorinated phenyl ring can be leveraged for spectroscopic observables such as fluorine-specific NMR signals. The D-stereocenter allows incorporation into peptides designed to resist enzymatic degradation or to alter binding orientation in biomolecular assays. Downstream derivatization after peptide assembly can enable generation of conjugation-ready analogs for biomolecule interaction studies and analytical characterization.
4. Protected Amino Acid Chemistry
Cbz-2,4,6-Trifluoro-D-Phenylalanine is suitable for protected amino acid synthesis strategies that require orthogonal handling of the nitrogen functionality. The Cbz carbamate provides a protecting group that can be removed under standard deprotection conditions to reveal the free amine for subsequent coupling, conjugation, or side-chain functionalization steps. The chiral D-configuration is preserved through protection and activation steps, supporting stereochemically consistent intermediate preparation for complex peptide and peptidomimetic assembly. The fluorinated aromatic ring remains intact under typical peptide synthesis conditions, enabling its use as a durable stereoelectronic element in multi-step synthetic sequences.
5. Process Chemistry Intermediate
Cbz-2,4,6-Trifluoro-D-Phenylalanine is relevant to process chemistry and fine chemical manufacturing where chiral, protected amino acid intermediates are required for scalable peptide-like syntheses. The presence of a single, well-defined stereocenter and a stable Cbz-protected amine simplifies route design for activation, coupling, and controlled deprotection steps in downstream manufacturing of fluorinated building blocks. The electron-poor fluorinated aromatic side chain can improve robustness of intermediates during purification and can be carried through iterative synthesis without introducing additional reactive heteroatoms. The compound thereby functions as a chiral intermediate that can be incorporated into larger manufacturing workflows producing fluorinated amino acid derivatives and peptide analogs for research and industrial chemical applications.
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