3,4-Dihydroxy-D-Phenylalanine is a D-configured, non-proteinogenic amino acid derivative featuring a benzyl side chain bearing two phenolic hydroxyl groups at the 3- and 4-positions. The molecule contains both an amino group and a carboxyl group on the α-carbon, and its catechol-like functionality enables hydrogen bonding and redox-active behavior typical of ortho-dihydroxy aromatic systems while remaining distinct from standard proteinogenic aromatic amino acids. In research settings, it is used as a defined building block for peptide and peptidomimetic synthesis and for structure-activity or chemical biology studies where catechol-bearing side chains, metal-binding motifs, or hydroxyl-functional handles are required for conjugation and analytical method development.
CAT No: CP13602
3,4-Dihydroxy-D-Phenylalanine is a D-configured phenylalanine analogue bearing a catechol-type 3,4-dihydroxy substitution on the aromatic side chain, making it a chemically distinctive building block for redox-active and metal-binding chemistries. Its phenolic hydroxyls support strong hydrogen-bonding and coordination behavior, while the D-stereochemistry is commonly leveraged to tune stability and resistance to enzymatic recognition in peptide and material contexts. This reagent is frequently selected when researchers need a catechol-functional amino acid motif rather than a standard proteinogenic aromatic side chain.
1. Peptide Building Block Incorporation
3,4-Dihydroxy-D-Phenylalanine is used as a catechol-bearing amino acid building block for peptide synthesis and peptide analog development, particularly when a D-amino acid configuration is desired to modulate stereochemical stability and downstream degradation behavior. In custom peptide synthesis workflows, the 3,4-dihydroxy aromatic side chain provides a chemically rich handle for subsequent conjugation or surface immobilization steps, enabling catechol-mediated attachment strategies after peptide assembly. Researchers in chemical biology and biomaterials-focused peptide engineering often choose this motif to introduce strong adhesive/coordination functionality into short peptides, linkers, and functional peptide segments used for material coating, capture assays, or multicomponent constructs.
2. Biomaterial Surface Functionalization
3,4-Dihydroxy-D-Phenylalanine is applied in biomaterials research as a catechol-functional amino acid component for coating and surface modification approaches where catechol chemistry is used to promote adhesion and metal coordination. Materials scientists and surface-chemistry groups incorporate this D-catechol amino acid motif into polymer backbones, surface-grafted layers, or peptide-based coatings to create interfaces with tunable binding to inorganic surfaces and metal ions. The presence of two adjacent phenolic hydroxyl groups supports robust intermolecular interactions that are useful in developing functional coatings for biosensor platforms, biointerface studies, and engineered material surfaces where stable attachment chemistry is required.
3. Metal Coordination And Chelation Studies
3,4-Dihydroxy-D-Phenylalanine is widely used as a defined catechol-containing ligand for studying metal coordination behavior and for preparing reference materials in coordination chemistry and analytical method development. Researchers use its catechol-type 3,4-dihydroxy motif to evaluate binding stoichiometry, complex formation trends, and ligand exchange under controlled conditions, including in experiments designed to compare catechol analogs and stereochemical variants. In analytical workflows, the compound can also serve as a chemically characterized standard for method development related to phenolic/chelation-sensitive assays, where reproducible catechol functionality is required to benchmark extraction, derivatization, or detection performance.
4. Enzyme Resistance Design Probes
3,4-Dihydroxy-D-Phenylalanine is used in chemical biology for designing D-amino-acid-containing probes and peptide fragments intended to probe or control enzymatic processing that is sensitive to amino acid stereochemistry. By combining the D-configuration with a catechol side chain, researchers can create defined substrates or structural motifs that help distinguish stereochemical recognition effects from side-chain chemistry effects in protease- or peptidase-related studies. This makes the reagent useful for constructing mechanistic probe sets, stability-focused peptide analogs, and comparative studies where the goal is to understand how stereochemistry and catechol functionality jointly influence recognition, turnover, or persistence in experimental systems.
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