4-Phosphono-D-Phenylalanine is a D-configured, non-proteinogenic phenylalanine derivative bearing a phenyl side chain substituted at the para position with a phosphono group. The molecule contains both an amino group and a carboxyl group on the α-carbon framework while the side-chain phosphono substituent introduces a strongly polar, anionic-capable functionality that can participate in metal coordination and electrostatic interactions under appropriate conditions. As a chemically defined amino acid analogue, it is used in peptide and protein chemistry and chemical biology workflows for structure-activity studies, enzyme-substrate investigations involving phosphonate-bearing residues, and the preparation of more complex phosphono-functionalized amino acid and peptide derivatives.
CAT No: CP16402
4-Phosphono-D-Phenylalanine is a D-configured phenylalanine analog bearing a phosphonic acid functionality on the aromatic ring, providing a strongly anionic, metal-binding side group that is distinct from proteinogenic amino acids. This structure makes it a useful building block for constructing phosphonate-containing amino acid motifs in peptide and medicinal chemistry programs, as well as for preparing defined standards and probes where the phosphonic acid group must be retained. Researchers select this compound when they need a stereochemically defined, phosphonate-functionalized amino acid framework for downstream coupling, assay development, or analytical method work.
1. Phosphonate Peptide Building
4-Phosphono-D-Phenylalanine is used as a stereochemically defined amino acid building block to introduce a phosphonate-bearing aromatic residue into peptides and peptidomimetics. In custom peptide synthesis workflows, the phosphonic acid functionality is leveraged to mimic phosphorylated motifs while maintaining a stable, non-hydrolyzable phosphate surrogate character. Medicinal chemistry groups and peptide engineers commonly incorporate this residue into constrained or receptor-targeting sequences where the presence of a highly polar, metal-coordinating phosphonate group is required for binding studies, structure-activity relationship (SAR) evaluation, or mechanistic probing of phosphorylation-like interactions.
2. Medicinal Chemistry Phosphonate Analogues
4-Phosphono-D-Phenylalanine supports small-molecule and peptidomimetic intermediate development where phosphonate groups are used to tune binding interactions and physicochemical properties. Pharmaceutical intermediate development teams use this compound to access defined phosphonate-containing amino acid fragments for assembling analog libraries, including conjugation-ready or coupling-ready derivatives that preserve the phosphonic acid motif. The D-configuration and aromatic phosphonate substitution help chemists control stereochemical outcomes and electronic/charge presentation in SAR campaigns, particularly when a phosphonate functionality must remain intact through late-stage assembly and characterization.
3. Analytical Standards And LC-MS Workflows
4-Phosphono-D-Phenylalanine is commonly used to prepare analytical reference materials for chromatography and mass spectrometry method development, calibration, and identity confirmation of phosphonate-containing analytes. Because the phosphonic acid group contributes a characteristic ionization behavior and strong metal interactions, this compound is valuable for building retention-time and MS-response expectations for related phosphonate amino acid derivatives and peptide fragments. Analytical chemistry teams also employ it as a defined structural standard when developing targeted LC-MS/MS assays that quantify or monitor phosphonate-bearing species in complex matrices, ensuring that the measured signal corresponds to a known, stereochemically defined compound.
4. Metal-Binding Probe Development
4-Phosphono-D-Phenylalanine is applied in chemical biology and materials-adjacent research where phosphonic acid groups are used to coordinate metals and create defined binding environments. Researchers incorporate this residue or its derivatives into probe constructs or functional materials to exploit the strong affinity of phosphonate for metal ions, enabling controlled immobilization, affinity capture, or coordination-driven assembly. The combination of a D-amino acid framework with an aromatic phosphonate motif helps maintain structural definition during probe or material synthesis, which is particularly useful when downstream characterization requires reproducible charge density and metal-binding behavior.
3. Autoinhibition and phosphorylation-induced activation of phospholipase C-γ isozymes
5. Cationic cell-penetrating peptides are potent furin inhibitors
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