Fmoc-D-Tyr(PO3H2)-OH is an Fmoc-protected D-tyrosine derivative bearing a phosphonic acid substituent on the phenolic side chain, classifying it as a protected, non-standard amino acid suitable for peptide-related synthesis. The molecule contains an Fmoc carbamate protecting group on the α-amino function, a free carboxylic acid at the α-position, and a phosphonic acid (PO3H2) group that introduces strong anionic character and hydrogen-bonding capacity while retaining the tyrosine aromatic ring. In synthesis and chemical biology workflows, it is employed as a building block to introduce a tyrosine-phosphonate motif into peptide frameworks or peptide conjugates, and it can also serve as a substrate analogue for analytical or structure-activity studies that require a defined phosphonic acid functional handle.
CAT No: CP25479
CAS No:178432-30-9
Synonyms/Alias:Fmoc-D-Tyr(PO3H2)-OH;CHEMBL154506;178432-30-9;AmbotzFAA1694;SCHEMBL8933066;CTK8E9914;MolPort-008-267-722;ZINC2560018;BDBM50121966;RT-012956;N-alpha-(9-Fluorenylmethyloxycarbonyl)-D-phosphotyrosine;2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-(4-phosphonooxy-phenyl)-propionicacid
Chemical Name:N-alpha-(9-Fluorenylmethyloxycarbonyl)-D-phosphotyrosine
Fmoc-D-Tyr(PO3H2)-OH is a fluorenylmethoxycarbonyl (Fmoc) protected D-tyrosine derivative bearing a phosphonic acid group on the phenolic side chain, yielding an amino acid building block with a stereodefined chiral center. The molecule contains an Fmoc-protected α-amino functionality for base-labile peptide coupling, a free carboxylic acid for C-terminal activation chemistry, and a strongly acidic phosphonate (PO3H2) that can participate in hydrogen bonding and metal coordination while remaining compatible with protected-amino-acid workflows. The D-configuration at the amino acid stereocenter supports stereochemically controlled incorporation into peptides and peptidomimetics, while the phosphonic acid substituent provides a handle for phosphorylation-mimetic design and subsequent functional transformations. The presence of both protected amine and unprotected phosphonic acid makes the compound a practical intermediate for building phosphonate-containing scaffolds and for generating defined, charge-rich peptide analogs used in biochemical and materials-oriented synthesis.
1. Peptide Synthesis
Fmoc-D-Tyr(PO3H2)-OH is used in peptide synthesis as a protected amino acid building block for incorporation of a phosphonate-bearing tyrosine analog into linear peptides and peptide fragments. The Fmoc group enables standard base-mediated deprotection to reveal the α-amine for peptide coupling, while the carboxylic acid supports activation to form amide bonds at the growing chain terminus. The side-chain phosphonic acid (PO3H2) introduces an anionic, hydrogen-bonding functional group that can influence coupling conditions, solubility, and the conformational behavior of the resulting peptide. Downstream, the resulting phosphonate-containing peptides can serve as phosphorylation-mimetic probes or as defined substrates for biochemical assays that require a stable phosphonate surrogate rather than a labile phosphate ester.
2. Chemical Biology Probes
Fmoc-D-Tyr(PO3H2)-OH supports chemical biology research where phosphotyrosine recognition, phosphatase/substrate specificity, or kinase-related binding motifs are investigated using charge-defined analogs. The D-tyrosine stereochemistry provides stereocontrol for receptor or enzyme binding studies that are sensitive to side-chain geometry, while the phosphonic acid group provides a persistent negative charge state comparable to phosphorylated residues. The Fmoc-protected α-amine allows controlled incorporation into peptide-based probes, enabling systematic structure-activity relationship studies across peptide length and neighboring residue context. The resulting phosphonate analogs can be used to generate defined molecular recognition reagents for studying protein-ligand interactions, mapping binding determinants, and comparing recognition behavior under conditions where phosphate esters would be unstable.
3. Bioconjugation Chemistry
Fmoc-D-Tyr(PO3H2)-OH can be applied to bioconjugation workflows that require a phosphonic acid functionality as a strong, metal-coordinating or affinity-oriented handle on peptide conjugates. The phosphonate side chain can participate in coordination chemistry and electrostatic interactions, which may be leveraged to attach peptides to surfaces, capture biomolecular targets, or tune conjugate charge density for controlled binding behavior. The Fmoc-protected amino acid format enables incorporation into conjugation-ready peptide sequences, after which the phosphonic acid remains available for subsequent coupling or affinity-driven assembly steps. The stereodefined D-tyrosine residue can further help maintain structural integrity of the conjugate scaffold in systems where stereochemistry affects binding and proteolytic stability.
4. Peptidomimetics And SAR Studies
Fmoc-D-Tyr(PO3H2)-OH is suitable for peptidomimetic construction and structure-activity relationship (SAR) studies that target phosphotyrosine-like pharmacophores with improved chemical stability. The amino acid backbone and protected Fmoc group allow systematic generation of analog series through peptide coupling strategies, while the phosphonic acid substituent provides a stable, strongly acidic mimic of phosphorylated tyrosine. The D-configuration supports stereochemical differentiation between enantiomeric analogs, enabling SAR comparisons that probe how stereochemistry and side-chain charge distribution affect molecular recognition. The resulting phosphonate-containing peptidomimetics can be used as defined fragments in medicinal chemistry programs and as reference standards for analytical evaluation of analog libraries.
5. Process Chemistry Intermediate
Fmoc-D-Tyr(PO3H2)-OH serves as a chiral, protected amino acid intermediate for industrial fine chemical synthesis routes that require incorporation of phosphonate functionality into peptide-grade or peptide-derived products. The Fmoc-protected amine supports scalable peptide-building workflows where base-triggered deprotection and subsequent coupling can be integrated into manufacturing sequences, while the free carboxylic acid enables controlled activation chemistry for chain extension. The phosphonic acid group, although strongly acidic, provides a robust functional motif for downstream conversion into salts, surface-active derivatives, or additional protected forms when process conditions require adjusted solubility and handling. The defined stereochemistry and functional group pattern make the compound compatible with process development for phosphonate-containing specialty chemicals, including research-grade reagents and peptide analog intermediates used in applied biochemical manufacturing contexts.
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