Boc-L-Tyr(PO3H2)-OH*DIPEA is a protected, amino acid derivative in which L-tyrosine is functionalized with a phosphonic acid (PO3H2) substituent on the aromatic ring and the α-amino group is masked as a Boc carbamate. The molecule contains a free carboxylic acid (-CO2H) and a phosphonic acid moiety that can exist in protonated states, while the Boc group provides chemoselective protection of the amino functionality; "*DIPEA" indicates association with diisopropylethylamine as a counterion/base form. This protected phosphonate-bearing tyrosine analogue is used as a building block for peptide and peptidomimetic synthesis where stepwise coupling requires amino protection, and where the phosphonic acid side chain provides a handle for studying phosphorylation-mimetic behavior, charge effects, or for subsequent derivatization in chemical biology and analytical assay development.
CAT No: CP25300
CAS No:131124-82-8
Synonyms/Alias:131124-82-8;BOC-L-TYR-OH2DIPEA;BOC-L-TYR(PO3H2)-OH2DIPEA
Chemical Name:N-alpha-t-Butyloxycarbonyl-L-phosphotyrosine disopropylethylamine
Boc-L-Tyr(PO3H2)-OH*DIPEA is a protected L-tyrosine derivative bearing a phosphonic acid side chain (PO3H2) and a Boc-protected amino group, provided as a DIPEA-associated salt/complex to support handling and coupling. The combination of a stable, protected backbone with a highly polar, anionic phosphonate functionality makes this building block particularly useful when preparing peptide segments that require phosphate-mimetic or phosphonate-containing motifs. In peptide and medicinal chemistry workflows, the Boc group supports controlled assembly of protected intermediates, while the phosphonate side chain enables downstream incorporation into phosphorylated/negatively charged structural features.
1. Phosphonate-Containing Peptides
Boc-L-Tyr(PO3H2)-OH*DIPEA is used in peptide synthesis to introduce a tyrosine-derived phosphonate functionality as a phosphate mimic or charged side-chain element. Researchers developing kinase-substrate analogs, receptor-binding motifs, or phospho-regulated peptide libraries rely on this building block to maintain the acidic character of the side chain during segment assembly. The Boc-protected amino group supports stepwise construction of peptide sequences in protected-intermediate workflows, while the PO3H2 substituent provides the polar handle needed for later biological or analytical evaluation of phospho-like behavior.
2. Medicinal Chemistry Phosphomimetics
Boc-L-Tyr(PO3H2)-OH*DIPEA serves as a practical amino acid building block for medicinal chemistry programs that require phosphomimetic fragments within peptidomimetics or constrained analogs. Medicinal chemists use this derivative to install a tyrosine-based, negatively charged side chain that can emulate the electrostatics of phosphorylated residues in structure-activity relationship (SAR) studies. The protected backbone and pre-installed phosphonate functionality streamline the preparation of analog series where maintaining the anionic character is critical for downstream binding studies, stability profiling, or formulation screening.
3. Protected Segment Intermediate Synthesis
Boc-L-Tyr(PO3H2)-OH*DIPEA is commonly selected as a protected segment intermediate when building larger, multi-functional peptide fragments that include a phosphonate-bearing residue. Custom peptide synthesis groups and process-focused peptide developers use the DIPEA-associated form to improve practical handling of the strongly polar phosphonate side chain during coupling and purification steps. This product is especially relevant for assembling sequences where the phosphonate must remain intact through protected-chemistry steps, enabling reliable downstream conversion into fully assembled targets for biochemical assays and analytical characterization.
4. Phosphorylation-Analog Screening Libraries
Boc-L-Tyr(PO3H2)-OH*DIPEA is applied in the generation of phosphorylation-analog peptide libraries used in chemical biology and protein interaction studies. Scientists often incorporate phosphonate-bearing tyrosine residues to create panels of peptides that probe recognition mechanisms involving negatively charged post-translational modification sites. The Boc-protected amino functionality supports controlled peptide assembly, while the PO3H2 side chain provides a reproducible, phosphate-mimetic motif that can be compared across library members using standardized analytical workflows such as LC-MS characterization of the assembled peptides.
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