Fmoc-D-Tyr(PO3Me2)-OH

Fmoc-D-Tyr(PO3Me2)-OH is a D-configured, Fmoc-protected tyrosine derivative bearing a dimethyl phosphate ester on the phenolic side chain, forming an anionic, phosphorylated aromatic functionality while retaining the amino acid backbone for peptide chemistry. The molecule combines an Fmoc carbamate at the α-amino position with a free carboxylic acid, enabling orthogonal protection and controlled coupling under standard protected amino acid conditions. The D-configuration at the stereogenic center supports stereochemically defined incorporation into peptide sequences and chiral fragment assemblies. The phosphate ester provides strong hydrogen-bonding and ionic character, while remaining a chemically addressable handle for subsequent conversion to other phosphate forms or for tuning polarity in downstream syntheses.

1. Peptide Synthesis

Fmoc-D-Tyr(PO3Me2)-OH supports peptide building block preparation for solid-phase peptide synthesis where a phosphorylated tyrosine side chain is required in a stereodefined context. The Fmoc group enables standard N-terminal protection during chain elongation, while the carboxylic acid participates in peptide coupling to form amide linkages without disrupting the side-chain phosphate ester. The dimethyl phosphate ester on the phenolic oxygen can be carried through coupling and cleavage conditions that preserve the phosphate functionality, allowing construction of phospho-tyrosine mimetics for biochemical research. The resulting D-phosphorylated tyrosine-containing peptides can be used to probe phosphorylation-dependent recognition and to generate defined peptide substrates for enzyme studies and receptor-binding assays.

2. Chemical Biology

Fmoc-D-Tyr(PO3Me2)-OH serves chemical biology workflows that require controlled installation of a phosphate-bearing aromatic side chain for studying phosphorylation recognition motifs. The tyrosine core provides a phenyl ring for aromatic interactions, while the dimethyl phosphate ester introduces a charge-rich functional group that can mimic phosphotyrosine electrostatics and hydrogen-bonding patterns. The Fmoc-protected amino acid format supports incorporation into peptides or peptidomimetics, enabling structure-activity relationship studies focused on how side-chain phosphorylation state and stereochemistry influence molecular recognition. Downstream conversion of the phosphate ester to alternative phosphate forms can be applied to generate analog panels for interrogating binding specificity and signaling-relevant interactions at the molecular level.

3. Peptidomimetics And SAR

Fmoc-D-Tyr(PO3Me2)-OH can be applied to peptidomimetic construction and medicinal chemistry-adjacent SAR studies where stereodefined phosphotyrosine analogs are used as scaffold elements. The D-amino acid stereocenter supports tuning backbone conformation and protease stability trends in peptide-like structures, while the phosphate ester provides a handle for polar surface area modulation and interaction mapping. The protected amino acid derivative format facilitates systematic variation of chain length, flanking residues, and phosphorylation presentation through repeatable peptide coupling chemistry. The resulting phospho-tyrosine-containing analogs can be used as defined fragments in molecular design campaigns to evaluate how side-chain phosphorylation geometry and charge distribution affect target engagement patterns.

4. Bioconjugation Chemistry

Fmoc-D-Tyr(PO3Me2)-OH supports bioconjugation strategies that rely on incorporating a phosphate-functional aromatic residue into carrier peptides or linker constructs. The phosphate ester can participate in downstream chemical transformations to adjust reactivity toward coupling chemistries, while the tyrosine aromatic unit can serve as an attachment point in conjugate architectures when incorporated into engineered peptides. The Fmoc-protected backbone enables preparation of conjugation-ready peptide segments with precise placement of the phosphorylated residue, supporting reproducible linker length and charge presentation. The resulting phospho-tyrosine-containing conjugates can be used to generate analytical standards, affinity probes, or labeled biomolecule fragments for biochemical research and biomolecule modification studies.

5. Process Chemistry Intermediate

Fmoc-D-Tyr(PO3Me2)-OH is suitable as a chiral, protected amino acid intermediate for fine chemical synthesis routes targeting phosphorylated amino acid derivatives and peptide building blocks. The orthogonal combination of an Fmoc-protected α-amino group and a dimethyl phosphate ester side chain enables manufacturing workflows that separate protection management from side-chain functional-group conversion steps. The stereodefined D-tyrosine backbone supports consistent chiral quality in downstream peptide or peptidomimetic production, while the phosphate ester provides a controlled intermediate state for later functional adjustments. The compound can be employed to prepare libraries of phosphorylated tyrosine analogs at scale for industrial chemical manufacturing of research reagents and specialty peptide intermediates.

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