2,3-Dihydroxy-DL-Phenylalanine is a DL (racemic) phenylalanine derivative bearing a benzyl side chain substituted with two hydroxyl groups at the 2- and 3-positions, classifying it as a hydroxylated aromatic amino acid. The molecule contains both an amino group and a carboxyl group characteristic of amino acid frameworks, while the catechol-like dihydroxy functionality provides a polar, hydrogen-bonding side chain that can participate in redox-active and metal-coordinating chemistry under appropriate conditions. As a non-standard amino acid building block, it is used in peptide and amino-acid-derivative synthesis and in chemical biology and analytical studies where hydroxylated aromatic residues, conjugation handles, or structure-property relationships are examined.
CAT No: CP13203
2,3-Dihydroxy-DL-Phenylalanine is a catechol-bearing phenylalanine derivative supplied as a DL mixture, featuring two adjacent hydroxyl groups on the aromatic ring alongside the amino acid functionality. This redox-active dihydroxy motif is widely leveraged in chemical biology and materials workflows where catechol-mediated binding and surface interactions are advantageous. Researchers also use this compound as a defined aromatic amino acid building block for preparing functionalized peptide fragments and for developing analytical references related to catechol-containing amino acid chemistry.
1. Catechol Surface Functionalization
2,3-Dihydroxy-DL-Phenylalanine is used to introduce a catechol functionality into polymer and biomaterials development, where catechol groups enable strong surface interactions on oxide and metal-containing substrates. Materials scientists and coatings developers commonly incorporate this amino acid derivative into surface modification strategies to generate stable attachment points for subsequent coupling steps, including grafting of biomolecules or polymer chains. The presence of two neighboring phenolic hydroxyls supports robust interfacial chemistry, making it a practical reagent when a defined amino acid-derived catechol anchor is required rather than using non-specific catechol small molecules.
2. Peptide Fragment Building Block
2,3-Dihydroxy-DL-Phenylalanine serves as a specialized amino acid building block for preparing peptide fragments or peptidomimetic structures that require a catechol-bearing aromatic side chain. Peptide chemistry groups use it to study how dihydroxy-substituted phenylalanine motifs influence local chemistry, including redox behavior and reactivity of phenolic groups during downstream conjugation or assay workflows. Because the material is provided as a DL mixture, it is often selected for synthetic screening, method development, or comparative studies where absolute stereochemistry at the amino acid center is not the primary variable, while the catechol functionality remains the key structural feature.
3. Chemical Biology Conjugation Studies
2,3-Dihydroxy-DL-Phenylalanine is frequently employed in chemical biology workflows that rely on catechol-mediated capture or coupling to surfaces and biomolecular scaffolds. Researchers use it to generate defined catechol-containing intermediates for immobilization, affinity-style attachment, or to build standardized reagents that mimic catechol-bearing amino acid chemistry in controlled experiments. The dihydroxybenzene motif provides a chemically recognizable handle for investigating how catechol availability and redox state affect conjugation outcomes, without requiring the use of larger, more complex catechol-containing biomolecules.
4. Analytical Reference and Method Development
2,3-Dihydroxy-DL-Phenylalanine is used as an analytical reference material for developing and validating workflows that monitor catechol-containing amino acid derivatives, including LC-based quantification and derivatization-dependent detection approaches. Analytical chemistry teams and metabolomics method developers select this compound when they need a chemically defined dihydroxy phenylalanine standard to evaluate recovery, chromatographic behavior, and derivatization performance. Its well-defined catechol motif makes it a useful reference for distinguishing dihydroxy-substituted aromatic amino acid species from non-catechol analogs in method development and routine quality control of research assays.
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