3,5-Diamino-L-tyrosine is an L-tyrosine-derived amino acid featuring the phenolic aromatic ring substituted with two additional amino groups at the 3- and 5-positions, resulting in a diamino-phenol side chain. The molecule contains both an amino group and a carboxyl group on the α-carbon framework, with the side-chain phenol retaining its hydrogen-bonding and protonation behavior while the extra primary amines provide multiple sites for electrostatic interactions and salt formation. As a nonstandard amino acid building block, it is used in peptide and peptide-analog synthesis and in structure-activity or chemical biology studies where increased side-chain basicity and multidentate functionality are used to probe binding, conjugation, or analytical labeling strategies.
CAT No: CP17801
3,5-Diamino-L-tyrosine is a tyrosine-derived amino acid bearing two additional amino substituents at the 3- and 5-positions on the aromatic ring, enabling strong side-chain functionalization beyond the native phenolic group. As an L-configured amino acid, it is frequently used as a non-proteinogenic aromatic building block in peptide and peptidomimetic synthesis, where the extra amines provide handles for further derivatization and for tuning charge and hydrogen-bonding patterns. The dual aniline-like functionality also makes it a useful reagent for constructing highly substituted aromatic motifs in chemical biology workflows that require controlled aromatic amination density.
1. Peptidomimetic Building Blocks
3,5-Diamino-L-tyrosine is used by peptide chemistry groups to incorporate a densely aminated aromatic side chain into peptide analogs and peptidomimetics. Researchers commonly select this building block when they want to introduce additional hydrogen-bonding capacity and tunable basicity at the aromatic position, enabling SAR (structure-activity relationship) studies where aromatic substitution pattern and side-chain electronics are key variables. The L-amino acid stereochemistry supports its use in standard protected-amino-acid coupling workflows to generate analogs for binding studies, receptor/ligand interaction mapping, and medicinal chemistry lead optimization, where aromatic amination can modulate local interactions without changing the peptide backbone framework.
2. Chemical Biology Conjugation Handles
3,5-Diamino-L-tyrosine is also used in chemical biology and bioconjugation research as a source of multiple primary amine functionalities on an aromatic scaffold. Teams developing labeled peptides, affinity reagents, or multivalent interaction probes leverage the extra ring amines to enable downstream coupling strategies that require amine-reactive chemistries, including attachment of linkers, polymer segments, or capture moieties. Because the amines are positioned on the aromatic ring rather than only on the backbone, the resulting conjugates can be engineered to present functional groups with defined spatial orientation relative to the tyrosine-derived scaffold, which is valuable when constructing multivalent probes for studying protein-ligand recognition or for building custom reagent libraries.
3. Medicinal Chemistry SAR Intermediates
3,5-Diamino-L-tyrosine serves as a specialized intermediate for medicinal chemistry programs that require substituted tyrosine analogs as defined structural probes. Medicinal chemistry and process development teams use this amino acid building block to prepare analog series where aromatic diamination is used to probe how increased aromatic substitution and added donor sites affect potency, selectivity trends, and physicochemical properties during lead refinement. In practical development workflows, the reagent's well-defined amino acid functionality supports its conversion into peptide-like scaffolds or constrained aromatic fragments, enabling consistent SAR generation across analog sets while maintaining a stable, reproducible substitution pattern for comparative studies.
4. Aromatic Amine Derivatization Platforms
3,5-Diamino-L-tyrosine is frequently employed as a starting material for generating aromatic amine-rich derivatives used in materials chemistry and specialty reagent development. Researchers use the dual ring amino groups to create further substituted aromatic motifs that can be carried into polymerizable units, crosslinker precursors, or surface-reactive intermediates where controlled introduction of primary amines is required. In these workflows, the tyrosine-derived backbone provides a convenient handle for sequential functionalization, allowing the aromatic diamine region to remain available for subsequent derivatization steps that build more complex functional architectures for research-grade materials and specialty chemical manufacturing.
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