2,3-Dihydroxy-D-Phenylalanine is a D-configured aromatic amino acid derivative featuring a phenyl ring bearing two hydroxyl substituents at the 2- and 3-positions along with the standard amino (α-amino) and carboxyl (α-carboxyl) functionalities. The catechol-like dihydroxy side chain introduces hydrogen-bonding and redox-active phenolic character while the D-stereocenter distinguishes it from the corresponding L-amino acid forms used in many peptide contexts. As a non-proteinogenic, side-chain-modified amino acid, it is used as a chemical building block for peptide and peptidomimetic synthesis and for structure-activity or labeling studies where phenolic functionality and stereochemical control are required.
CAT No: CP13202
2,3-Dihydroxy-D-Phenylalanine is a D-configured phenylalanine analogue bearing two hydroxyl substituents on the aromatic ring, enabling strong hydrogen-bonding and redox-relevant reactivity typical of catechol-like motifs. This amino acid derivative is frequently used in chemical biology and medicinal chemistry workflows where aromatic diol functionality is leveraged for selective derivatization, metal coordination, or incorporation into bioactive peptide/peptidomimetic structures. Its stereochemical definition and dihydroxy substitution pattern make it a practical building block for constructing well-defined analogs and analytical standards.
1. Peptidomimetic Building Blocks
2,3-Dihydroxy-D-Phenylalanine is used as a defined amino acid building block for assembling peptides and peptidomimetics that require a dihydroxy-substituted aromatic side chain. Researchers in peptide drug discovery and structure-activity relationship studies incorporate this residue to introduce catechol-like hydrogen-bonding and specific physicochemical character into otherwise standard peptide backbones, supporting the development of analog series for binding and stability investigations. Because the compound is stereochemically specified as the D-enantiomer, it is also commonly selected when stereochemical control is needed to probe conformational effects or protease resistance trends in peptide analog design.
2. Chemical Biology Derivatization
2,3-Dihydroxy-D-Phenylalanine is applied in chemical biology workflows that use aromatic diol functionality for targeted derivatization and downstream conjugation chemistry. In practice, scientists employ this residue to generate well-characterized labeled or functionalized peptide fragments, or to introduce a dihydroxy aromatic handle into probe scaffolds used for studying biomolecular interactions and reaction environments. The two hydroxyl groups provide strong sites for controlled chemical modification, enabling reproducible preparation of intermediates for affinity reagents, detection tags, or mechanistic probe libraries where the side-chain functionality must be precisely defined.
3. Analytical Reference Standards
2,3-Dihydroxy-D-Phenylalanine is routinely used as an analytical standard and reference material for LC-MS and related quantification workflows involving catechol-like amino acid derivatives. Analytical teams use the defined D-stereochemistry and the characteristic dihydroxy substitution pattern to support method development, calibration, and identification of related analytes in complex matrices such as enzymatic reaction mixtures or metabolite-enriched extracts. The compound's unambiguous structure also makes it valuable for preparing retention-time and fragmentation benchmarks when monitoring aromatic diol-containing species in targeted assays.
4. Pharmaceutical Intermediate Development
2,3-Dihydroxy-D-Phenylalanine serves as a practical intermediate for medicinal chemistry and specialty chemical synthesis programs that require a stereochemically defined dihydroxyphenylalanine motif. Process and R&D chemists use it to access downstream analogs where the aromatic diol functionality is retained for further functional group interconversions or for building larger fragments used in peptidomimetic and small-molecule discovery campaigns. Its amino acid identity and defined stereochemistry help ensure consistent incorporation into synthetic sequences that demand structural fidelity from early intermediates through final compound assembly.
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