2,5-Dihydroxy-DL-Phenylalanine is a DL (racemic) phenylalanine derivative bearing a benzyl side chain substituted with two hydroxyl groups at the 2- and 5-positions, making it a non-standard, hydroxylated aromatic amino acid. The molecule contains both an amino group and a carboxyl group on the α-carbon framework, with the catechol-like dihydroxy functionality providing phenolic hydrogen-bonding and redox-active chemical behavior while the DL designation indicates mixed stereochemistry at the chiral center. As a structurally modified amino acid, it is used in peptide and amino acid derivative synthesis where the aromatic diol side chain can serve as a handle for further functionalization, and it can also be employed in analytical method development or structure-activity studies that compare hydroxylated aromatic side-chain effects.
CAT No: CP13403
2,5-Dihydroxy-DL-Phenylalanine is a racemic dihydroxy-substituted phenylalanine derivative featuring two phenolic hydroxyl groups on the aromatic ring. As a DL mixture, it is commonly used as a chemically defined building block for structure-property studies and for preparing catechol-like aromatic analogs where redox-active phenolic functionality is required. The presence of two hydroxyl groups makes it a useful precursor for downstream derivatization, polymer/biomaterial functionalization, and analytical method development targeting catechol-containing amino acid motifs.
1. Catechol Analog Synthesis
2,5-Dihydroxy-DL-Phenylalanine is frequently employed as a starting amino acid building block for preparing catechol-bearing aromatic intermediates used in medicinal chemistry and peptidomimetic development. Researchers use the two phenolic hydroxyl groups to access protected or functionalized catechol derivatives that can be incorporated into larger scaffolds, enabling systematic variation of aromatic substitution patterns while retaining hydroxyl-rich reactivity. Because the compound is supplied as a DL mixture, it is often selected for synthetic campaigns focused on chemical reactivity and derivatization rather than stereochemically pure structure.
2. Biomaterial And Surface Functionalization
2,5-Dihydroxy-DL-Phenylalanine is used in biomaterials research where catechol-like groups are leveraged to promote surface adhesion and to introduce reactive phenolic functionality into polymer or coating formulations. Materials scientists incorporate this amino acid derivative into chemical modification workflows to generate catechol-functional linkers or monomer units that can be used for constructing functional hydrogels, coatings, or immobilized biomolecule platforms. The dihydroxy substitution pattern supports targeted derivatization steps that translate the amino acid motif into material-grade functional chemistry for downstream coupling and surface attachment.
3. Analytical Standards For Phenolic Amino Acids
2,5-Dihydroxy-DL-Phenylalanine is applied as a reference material for analytical method development and calibration when quantifying phenolic amino acid analogs in complex matrices. Analytical chemists use the defined dihydroxy aromatic functionality to validate extraction, derivatization, and chromatographic or spectrometric readouts for catechol-containing species. The DL composition is particularly useful when the analytical workflow is designed to measure total abundance of the compound or related phenolic amino acid forms without requiring enantiomer-resolved quantitation.
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