4-(1-Pyrenyl)butyryl-Phe-OH is a phenylalanine-derived amino acid derivative in which the phenylalanine side chain is retained as an unprotected aromatic amino acid (Phe-OH) while the alpha-amino acid nitrogen is acylated with a 4-(1-pyrenyl)butyryl group bearing a 1-pyrenyl fluorophore. The molecule contains a carboxylic acid functional group and an amide linkage to the pyrenylbutyryl moiety, with the pyrene ring providing a hydrophobic, π-conjugated labeling handle that can participate in fluorescence-based detection and environment-sensitive photophysics. In synthetic and chemical biology workflows, this amide-linked, fluorophore-bearing phenylalanine analogue is used as a building block or labeling reagent for preparing fluorescent amino acid and peptide derivatives, supporting structure-function studies and analytical method development where a pyrene reporter is incorporated.
CAT No: CP26619
CAS No:199612-75-4
Synonyms/Alias:Py-Phe;199612-75-4;UNII-7U77MPQ0M2;N-4-(1-Pyrene)butyroyl-L-phenylalanine;7U77MPQ0M2;Py-Phe,Pba-Phe-OH;PY-PHE[MI];SCHEMBL4293091;CTK8E9954;ZINC2387209;N-(1-Pyrene)butyryl-L-phenylalanine;N-[4-(1-Pyrenyl)butyryl]phenylalanine;RT-014205;N-(1-Phenylalanine)-4-(1-pyrene)butyramide;N-(1-L-Phenylalanine)-4-(1-pyrene)butyramide;N-(1-Oxo-4-(1-pyrenyl)butyl)-L-phenylalanine;N-[1-oxo-4-(1-pyrenyl)butyl]-L-Phenylalanine,
4-(1-Pyrenyl)butyryl-Phe-OH is a phenylalanine derivative bearing a 1-pyrenyl fluorophore appended through a butyryl linker, providing a hydrophobic, strongly emissive tag for fluorescence-based studies. This structure is commonly leveraged as a labeled amino acid building block for preparing fluorescent peptides and for monitoring microenvironmental effects around the phenylalanine residue. The aromatic pyrene moiety enables sensitive excitation-dependent emission behavior, making the compound useful for assay development and mechanistic readouts in chemical biology and protein/peptide research workflows.
1. Fluorescent Peptide Probes
4-(1-Pyrenyl)butyryl-Phe-OH is used as a fluorescent amino acid building block to incorporate a pyrene reporter at or near a phenylalanine position within peptides. Researchers in chemical biology and peptide science rely on this labeled residue to create sequence-defined fluorescent peptides for studying folding, binding, and conformational changes in solution, where the pyrene emission responds to polarity and local environment. The butyryl spacer helps decouple the fluorophore from the peptide backbone, supporting more interpretable fluorescence changes when the peptide experiences hydrophobic or structural rearrangements during assay development.
2. Binding And Interaction Assays
4-(1-Pyrenyl)butyryl-Phe-OH supports fluorescence readouts in binding and interaction experiments where pyrene is used as a reporter for association events. In practice, peptide and protein interaction studies often employ pyrene-labeled phenylalanine-containing ligands to track changes in fluorescence intensity or spectral features upon complex formation with receptors, binding domains, or polymeric hosts. This derivative is particularly useful when researchers need a residue-level tag that can be positioned within a peptide scaffold to probe how aromatic side-chain context influences recognition and microenvironmental dynamics.
3. Structure-Function Studies
4-(1-Pyrenyl)butyryl-Phe-OH is applied in structure-function investigations that compare peptide variants differing at a phenylalanine site, allowing fluorescence to serve as a sensitive proxy for local structural organization. Protein engineering and peptide optimization groups frequently use pyrene-labeled residues to evaluate how sequence context, linker length, and surrounding chemistry affect conformational preferences, aggregation propensity, or exposure of hydrophobic regions. Because the pyrene group is strongly fluorescent, this compound is also used for mapping relative changes across a panel of analogs during iterative probe design and experimental screening.
4. Analytical Fluorescence Standards
4-(1-Pyrenyl)butyryl-Phe-OH is used to prepare fluorescence standards and calibration materials for instrument qualification and method development in fluorescence spectroscopy and related assay platforms. Analytical groups often incorporate this labeled amino acid into reference peptide constructs or use it directly as a stable fluorescent reference to verify excitation/emission performance, day-to-day instrument drift, and assay consistency. The defined pyrene fluorophore content and strong emission make it a practical standard component when developing quantitative fluorescence workflows for peptide and biomolecular systems.
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