Cbz-3-Trifluoromethyl-L-Phenylalanine is a Cbz-protected, L-configured phenylalanine derivative bearing a meta-trifluoromethyl substituent on the aromatic side chain, classifying it as a substituted aromatic amino acid suitable for peptide-related chemistry. The molecule contains an N-terminal benzyloxycarbonyl (Cbz) protecting group and a free carboxylic acid, with the side chain retaining a hydrophobic, electron-withdrawing CF3 functionality that can influence conformational preferences and intermolecular interactions during coupling and subsequent peptide assembly. In synthesis, the Cbz-protected amino acid is employed as a protected building block for stepwise peptide synthesis or for preparing substituted aromatic peptide analogues used in structure-activity studies, chemical biology probes, and analytical method development involving fluorinated amino acid motifs.
CAT No: CP16708
Cbz-3-Trifluoromethyl-L-Phenylalanine is an N-Cbz protected L-phenylalanine derivative bearing a 3-trifluoromethyl substituent on the aromatic ring, creating a chiral amino acid framework with a benzyloxycarbonyl-protected amine and a free carboxylic acid suitable for peptide coupling. The para/ meta substitution pattern places a strongly electron-withdrawing CF3 group on the phenyl side chain, which can modulate aromatic reactivity, hydrophobicity, and conformational preferences in peptide backbones. The Cbz carbamate provides orthogonal protection relative to typical carboxyl activation and supports controlled deprotection under hydrogenolysis conditions, while the stereogenic center retains L-configuration for stereochemically defined incorporation. The combination of protected amine, activated carboxyl functionality, and CF3-bearing aromatic side chain makes the compound a practical chiral intermediate for protected amino acid synthesis and downstream peptidomimetic construction.
1. Peptide Synthesis
Cbz-3-Trifluoromethyl-L-Phenylalanine is applied in peptide building and fragment coupling where an N-Cbz protected amino acid with a free carboxyl group enables standard peptide coupling chemistries to form amide bonds at the L-configuration stereocenter. The Cbz carbamate protects the α-amine during activation of the carboxylic acid and subsequent coupling, supporting stepwise assembly of protected peptide sequences. The CF3-substituted phenyl side chain functions as a chemically stable, hydrophobic aromatic element that can be incorporated into peptides to tune lipophilicity and metabolic stability in structure-activity relationship studies. The resulting CF3-aryl peptide analogs can be advanced to deprotection and further functionalization, aligning with peptide science workflows and synthetic methodology development.
2. Peptidomimetics And SAR
Cbz-3-Trifluoromethyl-L-Phenylalanine is used in peptidomimetic and SAR-focused medicinal chemistry campaigns to introduce a CF3-bearing aromatic residue as a defined steric and electronic motif. The protected amino acid format supports incorporation into peptide-like scaffolds while maintaining stereochemical control at the α-carbon. The electron-withdrawing CF3 group on the phenyl ring can influence hydrogen-bonding patterns, aromatic stacking, and local conformational behavior within constrained analogs, enabling systematic structure-activity relationship studies. Downstream synthetic utility includes conversion into longer analog series, side-chain-modified derivatives, and protected intermediates for iterative library synthesis.
3. Chiral Amino Acid Intermediate
Cbz-3-Trifluoromethyl-L-Phenylalanine serves as a chiral amino acid intermediate for stereoselective synthesis of fluorinated aromatic derivatives and amino acid derivatives requiring preserved L-configuration. The N-Cbz protection strategy allows selective transformations on the carboxyl group and side-chain region without perturbing the α-amine, supporting orthogonal protection/deprotection planning in multi-step routes. The CF3-substituted phenyl side chain provides a robust handle for later functional group interconversions, including aromatic derivatization strategies that retain the amino acid stereocenter. The compound can be employed to prepare protected amino acid building blocks for chemical manufacturing and fine chemical synthesis where reproducible stereochemical identity is required.
4. Side-Chain Functionalization
Cbz-3-Trifluoromethyl-L-Phenylalanine is utilized for side-chain functionalization strategies in synthetic organic chemistry where an aromatic CF3 group-bearing phenylalanine residue provides a stable, electronically tuned aryl platform. The Cbz-protected nitrogen enables controlled carboxyl activation and coupling while leaving the side-chain aromatic system available for subsequent derivatization steps in a protected context. The CF3 substituent can support downstream transformations that generate substituted aromatic motifs for molecular design, including analogs with altered hydrophobicity or altered binding-site interactions. The resulting functionalized amino acid derivatives can be carried forward into peptide analog construction, fragment elaboration, and scaffold diversification programs.
5. Pharmaceutical Intermediate Preparation
Cbz-3-Trifluoromethyl-L-Phenylalanine is suitable for pharmaceutical intermediate preparation in manufacturing-oriented synthetic sequences that require a protected amino acid building block with predictable handling and orthogonal functionality. The N-Cbz carbamate protects the amino group during carboxyl activation and coupling steps, aligning with process chemistry needs for robust protection strategies in multi-stage synthesis. The CF3-bearing aromatic side chain contributes a chemically stable fluorinated motif that can be carried through to final active or intermediate structures, supporting consistent impurity profiles across synthetic campaigns. Downstream utility includes conversion into CF3-containing peptide fragments, protected intermediates for medicinal chemistry scale-up, and well-defined chiral inputs for specialty chemical production.
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