4-Phosphono-L-Phenylalanine is a phosphono-substituted, proteinogenic amino acid derivative featuring an L-phenylalanine backbone with a phosphonic acid group on the para position of the phenyl side chain. The molecule contains a free amino group and a carboxyl group on the α-carbon, while the phosphonic acid substituent introduces a strongly acidic, metal-binding functionality that can participate in ionic interactions and coordination chemistry. It is used in peptide and protein-analog synthesis, chemical biology labeling, and structure-activity or binding studies where a phenylalanine-like scaffold bearing a phosphonate handle is needed for charge and coordination effects.
CAT No: CP16401
4-Phosphono-L-Phenylalanine is a phosphonate-bearing phenylalanine analog featuring a stereodefined L-amino acid backbone and a side-chain phosphonic acid functionality that is strongly suited for ionizable, metal-binding, and phosphate-mimetic chemistry. This reagent is used in chemical biology and medicinal chemistry workflows where phosphonate groups are leveraged to tune charge distribution and enable robust, reproducible interactions in enzyme and binding studies. Its defined amino acid framework also makes it a practical building block for downstream conjugation and incorporation into synthetic constructs.
1. Enzyme Inhibition Studies
4-Phosphono-L-Phenylalanine is frequently used by enzymology and chemical biology groups to probe active-site recognition in systems that accommodate phosphate or phosphonate motifs. Researchers employ the phosphonate functionality as a phosphate mimic to evaluate how charge and hydrogen-bonding patterns influence substrate binding and catalytic turnover, while the L-phenylalanine scaffold provides a defined amino acid context for structure-activity relationship (SAR) work. In practice, it is commonly selected for comparative studies alongside non-phosphorylated analogs to help distinguish contributions from the phosphonate group versus the aromatic amino acid portion.
2. Phosphonate Peptide And Conjugates
4-Phosphono-L-Phenylalanine is used as a functional amino acid building block for preparing phosphonate-containing peptides, peptide mimetics, and amino-acid-based conjugates. The presence of both an amino acid handle and a phosphonic acid group supports incorporation into synthetic sequences where a stable, ionizable phosphonate moiety is required for downstream assays, affinity capture, or controlled presentation of negative charge. This makes the compound a common choice for researchers developing phosphonate-decorated probes, affinity reagents, and biomolecule conjugates intended for studying phosphorylation-like recognition events or for creating defined chemical microenvironments.
3. Analytical Standards For Phosphonate Chemistry
4-Phosphono-L-Phenylalanine is applied as a reference material in analytical method development and characterization of phosphonate-bearing amino acid derivatives. Analytical chemists use it to validate LC-MS workflows, confirm retention behavior and ionization response for phosphonate species, and support calibration or qualification of phosphonate-containing standards in complex matrices. Its defined structure and strong ionizable phosphonic acid group make it particularly useful when distinguishing phosphonate signals from closely related carboxylate-bearing analogs in method qualification and routine analytical checks.
4. Medicinal Chemistry SAR Building Block
4-Phosphono-L-Phenylalanine is used in medicinal chemistry programs to generate and evaluate phosphonate-substituted analog series that target phosphate-binding pockets or require a persistent negative charge element. Medicinal chemists often select this scaffold to systematically vary the phosphonate environment while maintaining an amino-acid-like aromatic core for consistent structural comparison across analogs. In downstream development, it serves as a practical intermediate precursor for constructing phosphonate-containing small molecules and peptidomimetic fragments used in binding and selectivity screening workflows.
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