2,5-Dihydroxy-D-Phenylalanine is a D-configuration aromatic amino acid bearing a phenyl side chain substituted with two hydroxyl groups at the 2- and 5-positions, making it a modified, proteinogenic-analog class amino acid suitable for peptide and structure-activity studies. The molecule contains a free amino group and a carboxyl group characteristic of amino acids, while the catechol-like dihydroxy functionality provides phenolic hydrogen-bonding and metal-coordination behavior that can influence conjugation and sequence-dependent properties. As an amino acid building block, it is used in chemical synthesis and in the preparation of peptide derivatives where the additional hydroxyl pattern supports targeted functionalization, analytical differentiation, and comparative studies of how aromatic diol substitution affects peptide structure and reactivity.
CAT No: CP13402
2,5-Dihydroxy-D-Phenylalanine is a D-configured aromatic amino acid featuring two phenolic hydroxyl groups on the side chain, enabling strong hydrogen-bonding and straightforward derivatization of the catechol-like functionality. This hydroxyl-rich scaffold makes it a useful building block for chemical biology and materials-oriented synthesis where redox-reactive or metal-binding catechol motifs are leveraged, while the D-stereochemistry supports incorporation into non-native peptide contexts and stereochemically defined analogs.
1. Peptidomimetic Building Block
2,5-Dihydroxy-D-Phenylalanine is used by peptide and peptidomimetic researchers to introduce a stereodefined, hydroxylated aromatic residue into short peptides, cyclic scaffolds, and side-chain functional analogs. The D-configuration supports the preparation of non-proteinogenic sequences for structure-activity relationship studies and for probing how stereochemistry influences conformation and stability in synthetic peptide systems. The two phenolic hydroxyl groups provide a practical handle for downstream conjugation or for installing additional functional features on the aromatic ring after peptide assembly.
2. Bioconjugation And Surface Chemistry
2,5-Dihydroxy-D-Phenylalanine is commonly selected for bioconjugation workflows and biomaterials surface functionalization where catechol-like groups are used to promote strong surface interactions and enable robust attachment strategies. Researchers use this residue to build catechol-bearing linkers for coating polymers, functionalizing nanoparticles, or preparing reactive intermediates that can be coupled to proteins, peptides, or material surfaces through subsequent derivatization steps. The presence of two hydroxyl groups supports predictable chemical modification routes and helps generate conjugates with improved retention at interfaces compared with mono-hydroxyl aromatic motifs.
3. Metal-Binding Chelation Probes
2,5-Dihydroxy-D-Phenylalanine is applied in chemical biology and analytical chemistry to construct metal-binding motifs for probe development and coordination-based assay formats. The adjacent phenolic hydroxyl pattern supports chelation behavior that can be exploited to tune binding of metal ions or to generate coordination complexes used as reporters in solution-phase studies. In practice, this amino acid is incorporated into defined ligands or used as a building block for preparing coordination-capable standards and reagents where stereochemical control (D-configuration) helps maintain consistent structural presentation in the assembled probe.
4. Analytical Standard And Derivatization Reagent
2,5-Dihydroxy-D-Phenylalanine is also used as a reference material and derivatization reagent in analytical method development targeting catechol-containing amino acid motifs. Laboratories employ it to validate chromatographic behavior, retention characteristics, and derivatization consistency for hydroxylated aromatic analytes in LC-based workflows. Because the compound contains two phenolic hydroxyl groups, it is a convenient starting point for generating chemically consistent standards or calibration components for assays that rely on controlled functional group derivatization.
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