4-Phosphonomethyl-L-Phenylalanine is an L-phenylalanine derivative bearing a phosphonomethyl substituent at the para position of the phenyl side chain, classifying it as a non-standard, functionalized amino acid for peptide and chemical biology workflows. The molecule contains a primary amino group and a carboxyl group on the amino acid backbone while the side-chain substituent introduces a phosphonic acid functionality capable of existing in protonated and salt forms, with the L stereochemistry indicated in the product name. As a chemically defined building block, it is used to introduce a charged, phosphate-like handle into peptide analogues and to support studies of phosphorylation-mimetic interactions, enzyme-substrate recognition, or structure-activity relationships in systems where a phosphonate-bearing aromatic side chain is required.
CAT No: CP16501
CAS No:142434-81-9
Synonyms/Alias:4-Phosphonomethyl-L-phenylalanine;142434-81-9;(2S)-2-amino-3-[4-(phosphonomethyl)phenyl]propanoicacid;4-Phosphonomethylphenylalanine;AmbotzHAA7140;4-Phosphonomethyl-L-phe;Phenylalanine,4-(phosphonomethyl)-,hydrochloride(9CI);AC1L2QR0;2-AMINO-3-(4-PHOSPHONOMETHYL-PHENYL)-PROPIONICACID;SCHEMBL738555;p-(Phosphonomethyl)phenylalanine;CTK4A8907;MolPort-008-268-076;ZINC1550959;AM83477;L-Phenylalanine,4-(phosphonomethyl)-;AM005172;KB-40296;KB-239143;TX-013215
4-Phosphonomethyl-L-Phenylalanine is an L-phenylalanine derivative bearing a phosphonomethyl substituent on the side chain, providing a strongly anionic, phosphate-mimicking functionality that is widely used in chemical biology and medicinal chemistry research. Its phosphonate group enables robust ionic interactions and makes the compound a useful building block for designing phosphonate-containing analogs, including enzyme inhibitors and receptor-binding ligands. The amino acid backbone supports downstream incorporation into synthetic sequences where amino acid-derived stereochemistry and side-chain functionality are both required.
1. Enzyme Inhibitor Building Block
4-Phosphonomethyl-L-Phenylalanine is used as a key amino acid building block for preparing phosphonate-containing inhibitor candidates targeting enzymes that recognize carboxylate or phosphate-like motifs. Medicinal chemistry groups employ this derivative to construct analog series where the phosphonomethyl group serves as a stable, charge-rich functional mimic, while the L-configuration of the amino acid framework supports consistent stereochemical presentation in the final inhibitor scaffold. This makes it particularly relevant for inhibitor design workflows that require precise side-chain placement and reliable chemical stability of the phosphonate functionality during lead optimization.
2. Peptidomimetic And Ligand Synthesis
4-Phosphonomethyl-L-Phenylalanine is commonly incorporated into peptidomimetic and ligand synthesis programs where amino-acid-derived geometry is used to control the spatial arrangement of functional groups. Researchers in chemical biology and drug discovery use it to generate phosphonate-bearing analogs that can engage binding sites through strong electrostatic and hydrogen-bonding interactions, while the phenylalanine backbone provides a rigid hydrophobic element for tuning binding pocket complementarity. In downstream development, the compound is valued as a stereodefined precursor for assembling complex structures that retain a phosphate-mimic pharmacophore without relying on labile phosphate esters.
3. Phosphonate-Containing Conjugates
4-Phosphonomethyl-L-Phenylalanine is leveraged in the preparation of phosphonate-functionalized conjugates used to probe or modulate biomolecular recognition processes. Chemical biology laboratories use phosphonomethyl-bearing amino acid derivatives to introduce a persistent, negatively charged handle into larger constructs such as affinity ligands, immobilizable building blocks, or structured molecular probes. The phosphonate functionality supports stable incorporation into synthetic architectures where maintaining strong anionic character is essential for reproducible binding behavior and for maintaining performance under conditions that would compromise more hydrolytically sensitive phosphate forms.
4. Analytical Standard Development
4-Phosphonomethyl-L-Phenylalanine is also used as a reference material in analytical method development and characterization of phosphonate-containing compounds. Analytical chemistry teams employ it to support LC-MS workflows that require structurally defined standards for phosphonomethyl/amino acid-derived species, including studies that monitor synthesis progress, purity, or stability of phosphonate-bearing intermediates and final products. Because it combines an amino acid backbone with a distinct phosphonate motif, it is particularly useful for confirming identity and for method calibration when phosphonate-containing analytes are expected to show characteristic ionization behavior in mass spectrometric detection.
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