2,6-Dihydroxy-D-Phenylalanine is a D-configured amino acid derivative of phenylalanine in which the aromatic ring bears two hydroxyl substituents at the 2- and 6-positions, defining its catechol-like side-chain functionality. The molecule contains an amino group and a carboxyl group characteristic of amino acids, while the dihydroxy aromatic side chain can participate in hydrogen bonding and redox-active chemistry typical of catechol motifs, with the D stereochemical configuration indicated by the product name. In peptide and protein chemistry, this amino acid can be used as a structural building block for incorporating a hydroxylated aromatic residue into peptide analogues for structure-activity studies, chemical biology labeling strategies, and analytical method development where catechol-bearing side chains are required.
CAT No: CP13502
2,6-Dihydroxy-D-Phenylalanine is a D-configured, non-proteinogenic amino acid featuring a catechol-like 2,6-dihydroxy substitution on the phenyl side chain and a free amino and carboxyl functionality. Its aromatic diol motif makes it a useful building block for redox-active and metal-binding chemical biology studies, as well as for preparing specialized peptide and small-molecule derivatives where catechol chemistry is required. Researchers also leverage the D-stereochemistry to probe stereochemical effects in peptide frameworks and to access non-natural analogs for structure-property investigations.
1. Catechol-Based Metal Binding
2,6-Dihydroxy-D-Phenylalanine is used in chemical biology and biomaterials research to introduce a catechol-like diol functionality that can coordinate metal ions and support metal-mediated assembly strategies. Teams working on surface chemistry, coating formulations, and coordination-driven materials commonly incorporate this amino acid into peptide or polymer segments to create metal-binding sites with defined stereochemistry. The D-configuration helps maintain non-natural stereochemical patterns in the resulting constructs, which is valuable when comparing binding behavior and stability across stereochemical variants.
2. Peptide Building Block Incorporation
2,6-Dihydroxy-D-Phenylalanine serves as a specialized amino acid building block for preparing modified peptides where the 2,6-dihydroxy aromatic side chain is required for downstream functionalization or interaction studies. Peptide chemists use it to generate non-natural peptide analogs for structure-activity relationship work, including studies that evaluate how catechol-like motifs influence conformation, aggregation propensity, or binding to metal-containing targets. Because the side chain contains two phenolic hydroxyl groups, it can also be leveraged in peptide post-modification workflows that rely on catechol reactivity, enabling access to tailored peptide conjugates.
3. Redox-Active Linker Development
2,6-Dihydroxy-D-Phenylalanine is applied in materials and chemical synthesis programs that require redox-active catechol functionality for constructing linkers, crosslinkable motifs, or redox-responsive materials. Researchers designing dynamic networks and reversible coupling chemistries often select catechol-bearing amino acid units to introduce a diol handle that participates in oxidation-state-dependent chemistry during material formation or processing. The amino acid form provides a convenient platform for integrating the catechol functionality into larger architectures, including peptide-derived scaffolds and amino-acid-based specialty polymers.
4. Analytical Reference for Catechol Chemistry
2,6-Dihydroxy-D-Phenylalanine is also used as a reference material in analytical method development and characterization workflows targeting catechol-containing amino acid derivatives. Analytical chemists employ it to validate sample preparation, chromatographic behavior, and derivatization strategies for dihydroxy-substituted aromatic amino acids, especially when monitoring catechol oxidation or quantifying diol-bearing species. Its defined D-stereochemistry and consistent functional group pattern make it useful for distinguishing stereochemical or structural variants in LC-MS and related analytical pipelines focused on catechol-modified building blocks.
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