Cbz-4-Trifluoromethyl-D-Phenylalanine is a Cbz-protected, D-configured phenylalanine derivative bearing a 4-trifluoromethyl substituent on the aromatic side chain, placing it in the class of unnatural amino acid analogues used for peptide chemistry. The molecule contains an N-Cbz carbobenzyloxy protecting group on the amino functionality and an unprotected carboxylic acid, while the side chain features a substituted benzyl group with a strongly electron-withdrawing CF3 substituent that modulates hydrophobicity and aromatic character. As a protected amino acid building block, it is employed in peptide synthesis workflows to introduce the CF3-bearing D-phenylalanine residue with controlled chemoselectivity at the amine during stepwise coupling and subsequent deprotection to generate the free amino group for incorporation into larger peptide frameworks.
CAT No: CP16809
Cbz-4-Trifluoromethyl-D-Phenylalanine is a D-configuration phenylalanine derivative bearing a benzyloxycarbonyl (Cbz) protecting group on the amino functionality and a 4-(trifluoromethyl) substituent on the aromatic ring. The molecule therefore combines a stereogenic α-carbon with a protected amine and a side-chain carboxylic acid, enabling controlled peptide coupling after appropriate activation of the acid. The electron-withdrawing trifluoromethyl group modulates aromatic reactivity and can influence conformational preferences in peptide-like scaffolds, while the Cbz group supports orthogonal protection strategies compatible with common peptide synthesis conditions. As a chiral amino acid intermediate, Cbz-4-Trifluoromethyl-D-Phenylalanine can be used to introduce a defined stereochemical element and a fluorinated aryl side chain into downstream peptide fragments, peptidomimetics, and structure-focused synthetic targets.
1. Peptide Synthesis
Cbz-4-Trifluoromethyl-D-Phenylalanine is applied in peptide building-block preparation where the Cbz-protected amine and carboxylic acid define a coupling-ready amino acid unit. The D-stereochemistry at the α-carbon supports stereocontrolled incorporation into peptide sequences, while the 4-trifluoromethyl phenyl side chain provides a fluorinated aromatic motif that can be retained through standard amide bond formation. The Cbz group can be managed through deprotection and re-protection workflows to align with N-terminal or internal residue placement during stepwise assembly. Downstream peptide fragments and peptide analogs constructed from this protected amino acid can serve as defined stereochemical probes for synthetic methodology development and scaffold diversification in peptide science.
2. Peptidomimetics And SAR
Cbz-4-Trifluoromethyl-D-Phenylalanine is used in peptidomimetic and structure-activity relationship studies where a fluorinated aromatic side chain is incorporated to tune physicochemical properties and molecular recognition patterns. The protected amino acid format supports conversion into amide-linked motifs that mimic peptide backbones while preserving the D-configuration for stereochemical interrogation. The trifluoromethyl group can influence aromatic electronics and hydrophobic character, enabling systematic comparisons across analog series prepared by controlled substitution at the phenyl ring. The resulting peptidomimetic intermediates and final analogs can be applied as SAR-focused chemical entities and as reference standards for analytical characterization of structure-defined fluorinated scaffolds.
3. Chiral Building Block Chemistry
Cbz-4-Trifluoromethyl-D-Phenylalanine functions as a chiral amino acid intermediate for stereoselective synthesis planning in fine chemical and research organic chemistry. The D-phenylalanine core provides a fixed stereocenter that can be carried through derivatization steps, while the Cbz-protected amine enables selective functional group transformations without premature amide formation. The 4-trifluoromethyl aromatic substituent provides a chemically distinctive handle for subsequent cross-coupling, electrophilic aromatic substitution, or scaffold elaboration depending on the protecting-group state. Downstream, the compound can be routed into fluorinated chiral fragments used for medicinal chemistry support, combinatorial library construction, and stereochemically defined intermediate preparation.
4. Protected Amino Acid Derivatization
Cbz-4-Trifluoromethyl-D-Phenylalanine is suitable for protected amino acid chemistry workflows that require orthogonal handling of the N-protecting group and the carboxylic acid functionality. The Cbz group supports controlled N-deprotection strategies that can be synchronized with peptide coupling cycles or with conversion of the acid into activated derivatives for subsequent coupling. The combination of a protected amine and a fluorinated aryl side chain supports selective generation of intermediates such as activated acid derivatives, coupling partners for fragment assembly, and protected residue forms for iterative synthesis. Downstream derivatization from this intermediate enables access to a range of stereodefined fluorinated amide products used in synthetic methodology development and biochemical research intermediate preparation.
5. Chemical Manufacturing Intermediates
Cbz-4-Trifluoromethyl-D-Phenylalanine is relevant to process chemistry and specialty chemical production as a defined stereochemical intermediate for manufacturing fluorinated peptide fragments and related amide-containing materials. The Cbz-protected amino acid structure supports established industrial protection/deprotection and coupling logic, allowing the D-configuration and trifluoromethyl aryl motif to be carried into higher-complexity products with controlled functional group timing. The presence of a single protected amine and a carboxylic acid provides a predictable functional-group profile for scale-up-oriented route design and for integration into modular synthesis of peptide-like building blocks. Downstream utility includes preparation of fluorinated chiral intermediates for research-grade fine chemicals, as well as feedstock for producing stereodefined amide scaffolds that can be further processed into specialty functional molecules.
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