3,5-Diamino-D-tyrosine is a non-proteinogenic, D-configured amino acid derivative related to tyrosine, featuring a phenolic aromatic ring bearing two additional amino substituents at the 3- and 5-positions relative to the hydroxyl group. The molecule contains both an amino group and a carboxyl group on the amino acid backbone, while the side chain presents a phenolic hydroxyl and two primary amine functionalities that can participate in protonation-state-dependent hydrogen bonding and ionic interactions. As a substituted aromatic amino acid, it is used as a building block for peptide synthesis and structure-activity studies where altered side-chain charge density, hydrogen-bonding patterns, or aromatic functionalization are required, including applications in chemical biology and analytical method development for labeled or modified peptide analogues.
CAT No: CP17802
3,5-Diamino-D-tyrosine is a D-configured tyrosine analog bearing two additional amino substituents on the aromatic ring, creating a strongly functionalized phenyl side chain with enhanced hydrogen-bonding and tunable reactivity compared with native tyrosine. This amino acid is frequently handled as a specialized building block for peptide and peptidomimetic synthesis where the aromatic diamino pattern is used to introduce defined side-chain chemistry for structure-activity studies and chemical biology workflows. Its stereochemical definition and dense side-chain functionality make it particularly useful when downstream conjugation, crosslinking chemistry, or binding-site mimicry requires more than a standard phenolic tyrosine handle.
1. Peptidomimetic Building Blocks
3,5-Diamino-D-tyrosine is used by peptide chemistry groups to construct peptidomimetics and non-natural peptide analogs that incorporate a D-amino acid backbone while presenting a highly substituted aromatic side chain. The 3,5-diamino substitution pattern supports side-chain-directed interactions in structure-activity relationship (SAR) studies, enabling researchers to probe how increased aromatic functionality influences conformation, local electrostatics, and recognition in receptor-binding or enzyme-binding assays. In custom peptide synthesis workflows, this residue is selected when a tyrosine-derived aromatic motif is needed but with additional amino functionality to better emulate or perturb specific binding-site contacts.
2. Chemical Biology Crosslinking Studies
3,5-Diamino-D-tyrosine is employed in chemical biology for designing peptide-based probes and interaction-mapping reagents where the aromatic diamino side chain provides a distinct chemical handle for downstream derivatization strategies. Researchers use this residue to introduce a defined, densely functionalized aromatic motif into peptides that can be further modified to support immobilization, capture chemistry, or targeted labeling schemes in protein interaction experiments. The D-configuration also helps some workflows manage enzymatic degradation during incubation periods, supporting the practical handling of peptide probes in complex experimental matrices.
3. Medicinal Chemistry SAR Probes
3,5-Diamino-D-tyrosine is used in medicinal chemistry and hit-to-lead optimization to generate conformationally and electronically distinct peptide-like scaffolds for SAR investigations. The additional amino groups on the aromatic ring allow medicinal chemists to systematically vary hydrogen-bonding capacity and aromatic side-chain electronics relative to standard tyrosine-derived residues, supporting focused studies on how side-chain patterning affects binding modes and structure-function relationships. In practice, this amino acid is selected when researchers want a tyrosine-inspired aromatic element but require a more information-rich substitution pattern to differentiate candidate analogs during lead refinement.
4. Analytical Derivatization Standards
3,5-Diamino-D-tyrosine is also used as a specialized reference material in analytical method development and derivatization optimization for assays targeting aromatic amino acid motifs with enhanced amino functionality. Laboratories preparing LC-MS or derivatization-based workflows may include this compound to evaluate recovery, derivatization efficiency, and chromatographic behavior of diamino-substituted aromatic residues. Because the compound is stereochemically defined and structurally distinct from common proteinogenic amino acids, it serves as a discriminating standard when confirming identity or monitoring chemical conversion steps in peptide-related analytical pipelines.
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