Cbz-2-Trifluoromethyl-D-Phenylalanine is a Cbz-protected, D-configured phenylalanine derivative bearing a 2-trifluoromethyl substituent on the alpha-carbon framework, placing a fluorinated, strongly electron-withdrawing group adjacent to the amino acid backbone. The molecule contains a carbamate-protected amino functionality (Cbz) and a free carboxylic acid group, while the side chain retains a benzyl-like aromatic moiety with the additional 2-CF3 substitution that can modulate polarity, steric profile, and conformational preferences in peptide-like structures. As a protected amino acid building block, it is used in peptide synthesis and related structure-activity or chemical biology studies where incorporation of a fluorinated, stereodefined phenylalanine analogue supports studies of fluorine effects, labeling strategies, or the preparation of more complex amino acid and peptide derivatives.
CAT No: CP16609
Cbz-2-Trifluoromethyl-D-Phenylalanine is a Cbz-protected D-phenylalanine derivative bearing a 2-trifluoromethyl substituent on the alpha carbon, creating a stereodefined chiral amino acid intermediate with increased fluorinated hydrophobicity. The structure contains a benzyloxycarbonyl (Cbz) carbamate on the amino group and a free carboxylic acid, enabling controlled peptide coupling while maintaining orthogonal protection during multi-step synthesis. The trifluoromethyl group and the phenyl side chain provide distinctive electronic and steric features that can influence amide formation kinetics, conformational preferences, and downstream physicochemical properties of resulting peptides or peptidomimetics. The combination of a removable Cbz group and a stable fluorinated side-chain motif makes the compound suitable for stereochemically defined amino acid derivatization and protected amino acid chemistry.
1. Protected Amino Acid Chemistry
Cbz-2-Trifluoromethyl-D-Phenylalanine supports protected amino acid synthesis workflows where orthogonal functional group handling is required for peptide building block preparation. The Cbz-protected amine and carboxylic acid enable standard peptide coupling strategies while preserving the D-configuration at the alpha stereocenter. The 2-trifluoromethyl substitution can be carried through coupling steps without requiring side-chain protection, allowing direct incorporation into amide linkages that later undergo Cbz deprotection when needed. The resulting fluorinated amino acid unit serves as a robust intermediate for constructing stereodefined peptide segments and for preparing downstream derivatives used in synthetic methodology studies and chiral intermediate libraries.
2. Peptide Synthesis
Cbz-2-Trifluoromethyl-D-Phenylalanine is suitable for peptide synthesis applications requiring a D-amino acid residue with a fluorinated alpha-substituted motif. The Cbz carbamate functions as an N-protecting group for controlled N-terminal chemistry, while the free acid participates in coupling to form amide bonds with compatible activated carboxyl derivatives. The phenyl side chain and the 2-trifluoromethyl group introduce steric bulk and strong electron-withdrawing character that can modulate peptide conformation and stability in peptidic scaffolds. Incorporation of this residue can be applied to generate peptide analogs for structure-activity relationship studies, conformational profiling, and synthetic access to fluorinated peptide fragments used in biochemical research.
3. Peptidomimetics And SAR
Cbz-2-Trifluoromethyl-D-Phenylalanine can be employed in peptidomimetic construction where alpha-substituted fluorinated amino acid elements are used to tune molecular recognition and metabolic stability proxies. The D-configuration and the fluorinated 2-trifluoromethyl substituent provide stereochemical and electronic control that can be translated into amide-containing scaffolds, including constrained or analog series designed for SAR studies. The Cbz-protected amine allows sequential assembly of longer analogs or late-stage introduction into fragments, supporting modular synthesis approaches used in medicinal chemistry research. Fluorinated amino acid incorporation from this intermediate can also enable preparation of reference standards and comparative analogs for analytical characterization of structure-property relationships.
4. Chemical Biology Labeling
Cbz-2-Trifluoromethyl-D-Phenylalanine supports chemical biology research where fluorinated amino acid residues are incorporated into peptides or protein-targeting conjugates for tracking and binding studies. The protected amine and carboxylic acid enable conversion into coupling-ready intermediates that can be assembled into labeled peptides, affinity probes, or biosynthetic building blocks. The trifluoromethyl group provides a chemically distinctive handle that can improve detectability in fluorine-aware analytical workflows and can influence local hydrophobic interactions in biomolecular recognition contexts. The stereodefined D-amino acid character can be used to probe stereochemical effects on binding or processing by enzymes, supporting mechanistic investigations using fluorinated peptide analogs.
5. Pharmaceutical Intermediate Preparation
Cbz-2-Trifluoromethyl-D-Phenylalanine is applicable to pharmaceutical intermediate preparation where fluorinated amino acid building blocks are required for manufacturing-grade peptidic or peptidomimetic intermediates. The Cbz carbamate protection strategy supports controlled deprotection timing, allowing downstream processing to generate defined N-termini or to integrate the residue into larger synthetic sequences. The presence of a single carboxylic acid and a stable fluorinated motif supports reliable conversion into activated derivatives for coupling steps during fine chemical synthesis and process chemistry. The resulting intermediate can be routed into peptide fragment production, enabling consistent stereochemical incorporation of a D-2-trifluoromethyl phenylalanine unit into downstream drug-like scaffolds and reference materials used in applied development chemistry.
6. Process Chemistry And Fine Synthesis
Cbz-2-Trifluoromethyl-D-Phenylalanine fits process chemistry and fine chemical synthesis use cases that require a chiral, protected amino acid intermediate with predictable functional group reactivity. The Cbz group provides a removable N-protection handle compatible with orthogonal stepwise assembly, while the carboxylic acid supports conversion to coupling partners under controlled activation conditions. The fluorinated alpha-substituent and phenyl side chain can influence crystallinity and solubility behavior, which are relevant considerations for scalable intermediate handling and purification planning. The compound can serve as a stereochemically defined component for manufacturing routes that produce fluorinated peptide building blocks, peptidomimetic fragments, and analytical reference materials for industrial chemical production and applied biochemical research.
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