4-Phosphono-DL-Phenylalanine contains a phenylalanine backbone bearing a para-phosphono substituent on the aromatic ring, classifying it as a non-natural, aromatic phosphonate amino acid derivative. The molecule presents both an amino group and a carboxyl group characteristic of amino acids, with the "DL" designation indicating a racemic mixture at the stereocenter and the phosphono group providing a strongly electron-withdrawing, anionic-capable functionality that can participate in metal coordination and ionic interactions. In synthetic and chemical biology workflows, it is used as a defined phosphonate-bearing amino acid building block for preparing modified peptides and peptidomimetics, and as a substrate or reference compound in analytical method development and structure-activity studies involving phosphonate-functionalized aromatic residues.
CAT No: CP16403
4-Phosphono-DL-Phenylalanine is a DL-phenylalanine derivative bearing a phosphono group, providing a strongly acidic, phosphate-mimetic functionality alongside the aromatic amino acid side chain. This combination makes the compound a useful building block for introducing phosphonate motifs into peptide and small-molecule frameworks, where the anionic phosphate-like group can be used to probe charge, hydrogen-bonding, and recognition features. In research workflows, its defined phosphono functionality supports downstream coupling to targets that require a stable, non-hydrolyzable phosphate mimic rather than a labile phosphate ester.
1. Phosphonate Peptide Building Block
4-Phosphono-DL-Phenylalanine is used as a phosphonate-containing amino acid building block for peptide synthesis and peptide analog preparation, particularly when a phosphate-mimicking side chain is required for structure-function studies. Researchers incorporate this residue into short peptides, protease-substrate mimics, and phosphorylation-pattern analogs to evaluate how anionic charge distribution and hydrogen-bonding interactions influence binding or recognition in chemical biology assays. The phosphono group provides a stable handle for maintaining the "phosphorylated" character of the side chain under conditions where phosphate esters may be susceptible to hydrolysis.
2. Enzyme Mechanism Mimicry
4-Phosphono-DL-Phenylalanine supports biochemical and mechanistic studies that employ non-hydrolyzable phosphate analogs to interrogate enzymes and binding partners associated with phosphorylated substrates. In inhibitor and substrate-mimic development, the phosphono functionality helps reproduce key electrostatic and coordination features of phosphate recognition while the aromatic phenylalanine side chain provides a defined hydrophobic/aromatic element for positioning within enzyme pockets. This makes the compound a practical reagent for developing phosphonate-based peptide or small-molecule probes used in enzymology workflows and binding characterization experiments.
3. Phosphonate-Ligand Intermediate
4-Phosphono-DL-Phenylalanine is widely used as a pharmaceutical intermediate and specialty chemical building block for constructing phosphonate-containing ligands and analogs in medicinal chemistry programs. The stable phosphono moiety enables the preparation of phosphonate derivatives used to explore structure-activity relationships where phosphate-like charge and metal-binding/interaction patterns are important. Synthetic teams value the amino acid backbone for providing a convenient, stereochemically defined precursor platform that can be further functionalized into phosphonate-bearing scaffolds for lead optimization and chemical probe generation.
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