Fmoc-4-phosphono-Phe(Bzl)-OH is an Fmoc-protected phenylalanine derivative bearing a phosphono substituent at the 4-position of the aromatic ring and a benzyl-protected side-chain carboxylate substituent on the phenylalanine side chain (Phe(Bzl)). The molecule contains the Fmoc carbamate protecting group on the α-amino function, a free carboxylic acid at the α-position, and a phosphonic acid functionality that can exist in anionic forms depending on pH, while the benzyl group provides hydrophobic masking of the specified side-chain functionality. As a protected, structurally modified amino acid building block, it is employed in peptide synthesis and related chemical biology workflows to introduce an aromatic phosphono motif and a controlled functional handle for subsequent conjugation, binding studies, or analytical method development.
Fmoc-4-phosphono-Phe(Bzl)-OH is an Fmoc-protected phenylalanine derivative bearing a benzyl-protected side-chain carboxylate (Bzl) and a phosphono substituent at the para position of the aromatic ring, forming a chiral amino acid building block suitable for peptide chemistry. The molecule contains an Fmoc carbamate for temporary N-protection, a free carboxylic acid for C-terminal activation, and a phosphonic acid functionality that can exist in partially deprotonated forms to support metal coordination and strong hydrogen-bonding interactions. The benzyl group on the side-chain carboxylate provides hydrophobic shielding and orthogonal deprotection behavior under hydrogenolysis conditions, while the aromatic phosphono group introduces an additional reactive handle for derivatization and downstream scaffold elaboration. The combination of protected amine, activated acid, and phosphono reactivity makes this compound a structurally defined intermediate for stereochemically controlled peptide and peptidomimetic construction.
1. Peptide Synthesis
Fmoc-4-phosphono-Phe(Bzl)-OH is applied in solid-phase and solution-phase peptide synthesis where Fmoc protection enables iterative N-terminal deprotection and coupling cycles. The protected amino acid framework presents a carboxylic acid for amide bond formation while the para-phosphono phenyl motif can influence coupling microenvironments through ionic interactions and metal binding during synthesis and purification. The benzyl-protected side-chain carboxylate supports orthogonal protection logic, allowing selective removal to reveal a reactive carboxylate for subsequent conjugation or further functionalization. The resulting peptide products can incorporate a phosphono-bearing aromatic residue for studying phosphorylation-mimetic behavior and aromatic side-chain recognition in peptide science and biochemical research.
2. Peptidomimetics And SAR
Fmoc-4-phosphono-Phe(Bzl)-OH serves in medicinal chemistry programs focused on peptidomimetic construction and structure-activity relationship studies where a phosphono-substituted phenylalanine can function as a phosphate-mimic motif. The stereodefined amino acid core supports incorporation into peptide analogs with controlled chiral presentation, while the phosphonic acid group can participate in electrostatic interactions and hydrogen-bond networks that are relevant to binding-site geometry. The Fmoc group enables systematic generation of analog series through controlled sequence assembly, and the benzyl-protected functionality can be managed to tune polarity and solubility during library synthesis. Downstream derivatives produced from the phosphono and deprotected carboxylate functionalities can be used to generate SAR panels and to probe how aromatic electronics and anionic charge distribution affect molecular recognition.
3. Chemical Biology Labeling
Fmoc-4-phosphono-Phe(Bzl)-OH is suitable for chemical biology workflows that require incorporation of a phosphono-bearing aromatic residue into probes, affinity tags, or enzyme-interaction peptides. The phosphonic acid functionality can be used to create binding interactions with metal-dependent targets or to support conjugation strategies that rely on anionic group reactivity and stable coordination behavior. The Fmoc-protected amino acid format facilitates site-specific placement within peptides, enabling controlled spatial positioning of the phosphono group relative to other functional residues. The benzyl-protected carboxylate can be selectively deprotected to provide a handle for further coupling to linkers, reporters, or biomolecule scaffolds, supporting downstream probe generation and mechanistic studies in protein- and enzyme-focused research.
4. Process Chemistry Intermediate
Fmoc-4-phosphono-Phe(Bzl)-OH is relevant to process chemistry and fine chemical synthesis as a chiral, protected amino acid intermediate that integrates orthogonal protecting groups for scalable peptide-building workflows. The Fmoc carbamate provides a controllable N-protection strategy compatible with standard deprotection/coupling sequences, while the phosphono group can be managed as a functional handle that may require pH- and ion-state control during manufacturing operations. The benzyl-protected carboxylate supports robust handling during synthesis and can be removed under hydrogenolysis conditions to furnish a free carboxylate for subsequent downstream steps. The defined stereochemistry and functional-group pattern make this material applicable to route design for producing phosphono-containing peptide intermediates and related peptidomimetic fragments used in specialty chemical production.
5. Analytical Standards for Phosphono Peptides
Fmoc-4-phosphono-Phe(Bzl)-OH can be employed in analytical research for preparing reference materials and calibration compounds involving phosphono-substituted peptide residues. The combination of an Fmoc-protected amino acid core and a phosphonic acid aromatic substituent enables construction of defined peptide standards that reflect specific charge states and coordination behavior relevant to LC-MS, CE, and chromatographic method development. The benzyl-protected functionality allows generation of matched protected and deprotected analogs, supporting method transfer and peak assignment across different derivatization states. Downstream peptide standards derived from this building block can support characterization of phosphonate-containing products, impurity profiling, and stereochemically consistent verification of peptide synthesis outcomes in biochemical research and industrial quality control contexts.
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