2,4-Dihydroxy-L-Phenylalanine is a naturally occurring, proteinogenic amino acid derivative classified as a hydroxy-substituted phenylalanine, featuring an L-configuration at the α-carbon and a benzyl side chain bearing hydroxyl groups at the 2- and 4-positions. The molecule contains a free α-amino group and a free carboxyl group, and its catechol-like dihydroxy aromatic functionality provides phenolic hydrogen-bonding and metal-coordination behavior while remaining compatible with standard amino acid handling in peptide chemistry. As a side-chain-functionalized amino acid, it is used in peptide synthesis and structure-activity or binding studies where aromatic hydroxyl groups are incorporated to probe hydrogen-bonding patterns, redox-sensitive motifs, or post-synthetic derivatization opportunities.
CAT No: CP13301
2,4-Dihydroxy-L-Phenylalanine is a proteinogenic amino acid analog featuring a catechol-type 2,4-dihydroxy substitution on the phenyl side chain, retaining the L-configuration at the α-carbon. This additional phenolic functionality makes it a useful building block for preparing catechol-containing peptides and for studying structure-function relationships where redox-active or metal-binding catechol motifs are incorporated. In synthetic and analytical workflows, the presence of two hydroxyl groups supports downstream derivatization and conjugation strategies while providing a distinct chemical signature for characterization of catechol-bearing targets.
1. Catechol Peptide Building Block
2,4-Dihydroxy-L-Phenylalanine is used to introduce a catechol-like aromatic side chain into peptide sequences for custom peptide synthesis, including mechanistic peptide studies and material-relevant peptide designs. Researchers select this residue when they want a defined dihydroxy substitution pattern on the phenyl ring to probe how phenolic groups influence local conformation, intermolecular interactions, and reactivity in peptide contexts. The L-stereochemistry supports consistent incorporation into peptide frameworks, while the two side-chain hydroxyl groups enable further functionalization of the resulting peptide for downstream conjugation or surface attachment workflows.
2. Protein Interaction And Binding Studies
2,4-Dihydroxy-L-Phenylalanine is applied in chemical biology and protein research to construct catechol-functional peptide ligands and small-molecule mimics used to interrogate binding processes involving aromatic dihydroxy motifs. In these workflows, the residue serves as a chemically defined handle to generate ligands with controlled phenolic substitution, supporting comparative studies of structure-activity relationships across related catechol analogs. By embedding the 2,4-dihydroxy pattern into a peptide scaffold, researchers can better attribute observed binding or assembly behavior to the specific arrangement of hydroxyl groups rather than to nonspecific aromatic effects.
3. Analytical Derivatization Standard
2,4-Dihydroxy-L-Phenylalanine is frequently used as an analytical reference material and derivatization substrate for method development and characterization of catechol-containing analytes. Laboratories use it to validate sample preparation and detection workflows where phenolic groups are derivatized to improve chromatographic behavior or to enable selective detection in LC methods. Its defined L-configuration and dihydroxy substitution provide a reproducible standard for monitoring derivatization performance and for supporting quantitative or semi-quantitative analyses of catechol-bearing compounds in complex matrices.
4. Biomaterials Surface Functionalization
2,4-Dihydroxy-L-Phenylalanine supports biomaterials development where catechol chemistry is leveraged to create functional surfaces and coatings. Formulators and materials scientists incorporate this amino acid motif into peptide-based adhesives, hydrogel components, or polymerizable intermediates to enable surface immobilization and interfacial assembly strategies driven by dihydroxy phenolic functionality. The residue's two hydroxyl groups provide a chemically specific basis for attaching or crosslinking catechol-bearing constructs, supporting reproducible fabrication of catechol-functional biomaterial platforms used in research-grade surface engineering.
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