Cbz-2,4,5-Trifluoro-D-Phenylalanine is a Cbz-protected, non-natural amino acid derivative featuring a D-phenylalanine backbone bearing three fluorine atoms at the 2, 4, and 5 positions of the aromatic side chain. The molecule contains an N-protecting benzyloxycarbonyl (Cbz) carbamate on the amino group and a free carboxylic acid, with the fluorinated phenyl ring providing increased electron-withdrawing character and altered hydrophobic and steric properties relative to unmodified phenylalanine. In peptide chemistry, this protected amino acid is employed as a building block for introducing a fluorinated, stereodefined aromatic residue into peptide sequences and for structure-activity or labeling studies where the modified aromatic electronics and side-chain properties are used to probe binding and conformational effects.
CAT No: CP16909
Cbz-2,4,5-Trifluoro-D-Phenylalanine is a chiral, N-Cbz protected phenylalanine derivative in which the D-configuration at the α-carbon is retained while the aromatic side chain bears three fluorine atoms at the 2, 4, and 5 positions. The molecule combines a benzyloxycarbonyl (Cbz) carbamate on the amino group with a carboxylic acid functionality typical of phenylalanine-derived peptide building blocks, enabling controlled N-protection and downstream coupling chemistry. The tri-fluorinated aromatic ring increases electron-withdrawing character and can modulate conformational preferences and reactivity during peptide assembly and subsequent derivatization. The presence of a single stereogenic center and a stable carbamate protecting group makes the compound suitable as a chiral amino acid intermediate and protected residue for stereodefined peptide construction and analytical reference materials.
1. Peptide Synthesis
Cbz-2,4,5-Trifluoro-D-Phenylalanine supports peptide coupling workflows in research and fine chemical synthesis by providing a protected amine (Cbz carbamate) and a carboxylic acid for amide bond formation. The D-stereochemistry at the α-carbon enables stereodefined incorporation into linear peptides and protected peptide fragments, while the tri-fluorinated phenyl side chain can be used to tune hydrophobicity, aromatic electronics, and potential binding-site interactions. Cbz protection is compatible with standard peptide assembly strategies that rely on selective deprotection to reveal the free amine at controlled stages. Resulting peptide analogs can be used for structure-activity relationship studies, conformational probing, and generation of fluorinated peptide building blocks for downstream materials and binding assays.
2. Peptidomimetics And SAR
Cbz-2,4,5-Trifluoro-D-Phenylalanine is applicable to peptidomimetic construction and structure-activity relationship studies where aromatic fluorination is used to modulate molecular recognition and metabolic stability proxies. The compound's D-phenylalanine backbone provides a stereochemically defined scaffold, and the 2,4,5-trifluoro substitution pattern introduces strong inductive effects that can alter hydrogen-bonding patterns and aromatic stacking behavior in analog series. Cbz protection allows the residue to be handled as a stable intermediate during fragment coupling, while the retained carboxyl functionality supports conversion into activated derivatives for sequential assembly. Fluorinated phenylalanine-containing analogs prepared from this residue can serve as SAR tools and as defined chemical probes in medicinal chemistry discovery campaigns.
3. Protected Amino Acid Chemistry
Cbz-2,4,5-Trifluoro-D-Phenylalanine serves as a chiral, N-protected amino acid intermediate for protected amino acid synthesis and stepwise functional group management. The Cbz carbamate can be removed under conditions that preserve the tri-fluorinated aromatic ring, enabling orthogonal access to the free amine for subsequent peptide coupling, conjugation, or derivatization. The α-carboxylic acid functionality enables transformation into coupling-ready forms while maintaining stereochemical integrity of the D-center. Downstream use includes preparation of fluorinated amino acid derivatives, protected peptide fragments, and chemically defined intermediates for process chemistry routes that require predictable protection/deprotection behavior.
4. Chemical Biology Probes
Cbz-2,4,5-Trifluoro-D-Phenylalanine can be employed in chemical biology research to generate fluorinated amino acid-containing probes for tracking, binding studies, and interaction mapping. The tri-fluorinated aromatic side chain provides a distinct electronic signature and can enhance detectability in NMR-based workflows, while the D-configuration supports incorporation into peptides that resist proteolytic degradation compared with corresponding L analogs. Cbz protection enables controlled installation into peptide scaffolds, after which deprotection and further functionalization can introduce handles for labeling or affinity capture. Fluorinated residues derived from this compound can be integrated into molecular probes used to interrogate receptor/target interactions, validate binding modes, and support mechanistic studies through chemically well-defined constructs.
5. Pharmaceutical Intermediate Preparation
Cbz-2,4,5-Trifluoro-D-Phenylalanine is suitable for pharmaceutical intermediate preparation and specialty chemical production where stereodefined fluorinated amino acid residues are needed for medicinal chemistry libraries and process development. The combination of a single chiral center, a stable Cbz-protected amine, and a carboxylic acid group aligns with manufacturing-oriented synthesis planning that uses protected amino acids as standardized inputs for peptide-like intermediates. The tri-fluorinated aromatic ring can be carried through synthetic sequences with minimal side reactions, supporting reproducible conversion into coupling-ready intermediates and downstream fluorinated analogs. Prepared derivatives can feed into fine chemical synthesis of fluorinated peptidomimetics, constrained scaffolds, and defined building blocks used across discovery-to-development chemistry programs.
6. Analytical Research Standards
Cbz-2,4,5-Trifluoro-D-Phenylalanine functions as an analytical research standard and reference intermediate for method development targeting fluorinated amino acid and peptide species. The Cbz-protected amine and carboxylic acid provide well-characterized chemical forms for LC-MS and NMR method calibration, while the 2,4,5-trifluorinated aromatic ring yields a distinctive spectroscopic pattern that can improve identification confidence. D-stereochemistry enables stereospecific discrimination when analyzing chiral amino acid derivatives or peptide hydrolysates containing D-phenylalanine residues. Analytical standards derived from this compound can support impurity profiling, stability studies of protected amino acid intermediates, and verification of stereochemical integrity in peptide building block manufacturing and peptide synthesis workflows.
1. An Open-label, Single-center, Safety and Efficacy Study of Eyelash Polygrowth Factor Serum
2. The spatiotemporal control of signalling and trafficking of the GLP-1R
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