3,5-Diamino-DL-tyrosine is a non-standard tyrosine analogue featuring a phenolic aromatic ring bearing two additional amino substituents at the 3- and 5-positions, classifying it as a substituted aromatic amino acid rather than a canonical proteinogenic residue. The molecule contains both an amino group and a carboxyl functional group on the α-carbon, with stereochemistry described as DL to indicate a racemic mixture of enantiomers, and the side chain includes a phenolic hydroxyl alongside the extra amino functionalities that can participate in hydrogen bonding and acid-base behavior. As an amino acid building block, it is used in peptide and peptidomimetic synthesis to introduce a highly functionalized aromatic side chain for structure-activity studies, chemical biology conjugation handles, and analytical method development involving derivatized amino acid standards.
CAT No: CP17803
3,5-Diamino-DL-tyrosine is a non-proteinogenic, tyrosine-derived diamino building block featuring a catechol-bearing aromatic ring with two additional amino substituents at the 3- and 5-positions, supplied as a DL mixture. Its strongly functionalized aromatic side chain makes it a useful scaffold for constructing highly substituted aromatic motifs in peptide-like and small-molecule architectures, as well as for preparing chemical biology reagents where multiple aniline-like sites enable further derivatization. Researchers typically select this compound when they need an amino-functionalized aromatic platform that can be incorporated into synthetic sequences or converted into downstream intermediates for conjugation and analytical studies.
1. Aromatic Building Block Synthesis
3,5-Diamino-DL-tyrosine is used as an advanced aromatic amino building block in the synthesis of substituted phenyl- and aniline-rich scaffolds for medicinal chemistry and chemical biology. Medicinal chemistry groups and specialty synthesis teams rely on its densely amino-functionalized ring to introduce multiple nitrogen functionalities into heteroaromatic or peptidomimetic frameworks, supporting structure-property exploration where aromatic substitution pattern is a key design variable. The DL stereochemical mixture is generally acceptable for workflows focused on aromatic substitution and subsequent coupling chemistry rather than stereodefined biological recognition.
2. Peptidomimetic And Analog Construction
3,5-Diamino-DL-tyrosine serves as a side-chain-rich residue precursor for constructing peptide analogs and peptide-like libraries that incorporate highly substituted aromatic elements. Peptide chemistry researchers use it when they want to embed an amino-substituted tyrosine-derived aromatic motif into synthetic sequences to probe how increased aromatic substitution and multiple amino groups influence conformation, solubility, and chemical reactivity of the resulting analogs. In custom peptide synthesis and library development, its functionalized ring provides a handle for later derivatization steps that can be used to generate series of related compounds from a common aromatic core.
3. Derivatization For Conjugation Handles
3,5-Diamino-DL-tyrosine is commonly employed as a precursor for generating multifunctional conjugation-ready intermediates in materials chemistry and bioconjugation-oriented reagent development. Chemical biology and biomaterials teams value the presence of multiple amino sites on the aromatic ring because they can be transformed into reactive derivatives for subsequent coupling to polymers, linkers, or carrier scaffolds used in assay reagent preparation. This amino-rich aromatic platform is particularly useful when downstream design benefits from introducing several functional groups from a single starting residue rather than relying on mono-functional aromatic precursors.
4. Analytical Standard And Method Development
3,5-Diamino-DL-tyrosine is used in analytical chemistry workflows as a defined, highly substituted tyrosine-derived reference material for method development and characterization of derivatized aromatic amino species. LC-MS and related analytical method developers may incorporate it into calibration or qualification strategies where aromatic diamino substitution patterns are expected to affect retention behavior, ionization, or derivatization efficiency. Because the compound is supplied as a DL mixture, it is typically treated as a chemical reference for aromatic amino functionality rather than as a stereospecific standard for chiral separation studies.
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