Cbz-3-Trifluoromethyl-D-Phenylalanine is a Cbz-protected, D-configuration amino acid derivative in the phenylalanine family, featuring a benzyl-protected amino group and a side chain bearing a 3-trifluoromethyl substituent on the aromatic ring. The molecule contains both an N-Cbz carbamate and a free carboxylic acid functionality, with the trifluoromethyl group imparting strong electron-withdrawing character that can influence aromatic hydrophobicity and conformational preferences in peptide contexts. It is used as a protected building block for preparing modified peptides and as a substrate analogue in structure-activity and binding studies where fluorinated aromatic side chains and controlled N-protection are required for chemoselective coupling and subsequent deprotection.
CAT No: CP16709
Cbz-3-Trifluoromethyl-D-Phenylalanine is a D-configured phenylalanine derivative bearing a benzyloxycarbonyl (Cbz) protecting group on the amino functionality and a 3-trifluoromethyl substituent on the aromatic ring. The molecule combines a stereogenic center at the alpha carbon with a strongly electron-withdrawing CF3 group that modulates aromatic reactivity, amide formation behavior, and downstream chemical selectivity. The Cbz carbamate provides acid-stable protection during peptide coupling while remaining compatible with hydrogenolysis-based deprotection strategies when conversion to a free amine is required. The resulting chiral, protected amino acid intermediate is suitable for incorporation into peptide building blocks and for generating fluorinated aromatic analogs used in synthetic and biochemical research workflows.
1. Peptide Synthesis
Cbz-3-Trifluoromethyl-D-Phenylalanine is applied in peptide building block preparation where Cbz-protected amine chemistry supports stepwise peptide coupling. The D-configuration at the alpha stereocenter and the CF3-substituted phenyl side chain introduce stereochemical and electronic features that can be retained through amide bond formation using standard protected amino acid strategies. The Cbz group can be removed under hydrogenolysis conditions to enable subsequent coupling cycles, supporting N-terminal and internal residue construction. Downstream peptide analogs derived from this residue can be used to probe backbone stereochemistry effects and aromatic fluorination impacts on conformational preferences and stability.
2. Peptidomimetics And SAR
Cbz-3-Trifluoromethyl-D-Phenylalanine is used in peptidomimetic construction and structure-activity relationship studies where the CF3-bearing aromatic side chain acts as a defined hydrophobic and electron-withdrawing pharmacophore surrogate. The protected amino acid form facilitates controlled incorporation into peptide-like scaffolds, enabling systematic variation of aromatic substitution patterns while maintaining the D-amino acid stereochemistry. The CF3 group can influence local dipole distribution and metabolic stability trends in fluorinated analog series, supporting rational design of analog libraries. Resulting fluorinated peptide mimetics can serve as chemical probes for SAR mapping and for evaluating how stereochemistry and side-chain electronics shape molecular recognition.
3. Chemical Biology Probes
Cbz-3-Trifluoromethyl-D-Phenylalanine is suitable for chemical biology research requiring stereodefined fluorinated amino acid residues for labeling, affinity reagents, or molecular recognition studies. The Cbz-protected nitrogen supports sequential derivatization to generate peptide conjugates or scaffold fragments that present a consistent chiral environment to binding partners. The CF3-substituted phenyl ring can function as a spectroscopically and chemically distinctive handle for analytical tracking and for tuning hydrophobic interactions in probe design. Downstream conjugates prepared from this residue can be used to study binding selectivity, competitive interactions, and structure-dependent behavior in biochemical assays.
4. Protected Amino Acid Chemistry
Cbz-3-Trifluoromethyl-D-Phenylalanine is employed as a chiral protected amino acid intermediate for N-protection strategy development and orthogonal protection planning in peptide synthesis. The Cbz carbamate provides a stable protecting group during coupling steps, while its hydrogenolysis compatibility supports conversion to a free amine for further chain extension or for generating alternative protected forms. The D-configuration helps maintain stereochemical integrity when building chiral peptide fragments and can be exploited for preparing enantiomerically defined libraries. The CF3-substituted aromatic side chain can also serve as a functional motif for downstream transformations that rely on controlled aromatic reactivity and robust amide chemistry.
5. Pharmaceutical Intermediate Preparation
Cbz-3-Trifluoromethyl-D-Phenylalanine is relevant to pharmaceutical intermediate preparation workflows where fluorinated amino acid residues are incorporated into peptide-like active ingredients or research-grade analogs. The protected amino acid format supports scalable synthetic routes that require reliable chemoselectivity for amide bond construction and for controlled deprotection timing. The CF3 group-bearing aromatic side chain can be carried through manufacturing as a stable substituent that maintains defined physicochemical characteristics in final intermediates. The resulting fluorinated peptide building blocks and downstream derivatives can be used in fine chemical synthesis programs that generate stereochemically defined intermediates for medicinal chemistry and process development.
6. Process Chemistry and Fine Chemical Synthesis
Cbz-3-Trifluoromethyl-D-Phenylalanine is utilized in process chemistry and fine chemical synthesis as a chiral intermediate that supports reproducible peptide coupling chemistry and controlled protection/deprotection cycles. The Cbz-protected amine and the stable carboxylate functionality enable integration into manufacturing routes for chiral amino acid derivatives and fluorinated aromatic analogs. The stereogenic center and CF3-substituted aromatic ring can help standardize intermediate identity across batches, supporting consistent downstream formation of peptide fragments and analytical reference materials. The compound thus functions as a practical feedstock for producing fluorinated amino acid derivatives and peptide building blocks used across industrial chemical manufacturing and applied synthetic methodology.
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