2,6-Dihydroxy-L-Phenylalanine is a naturally occurring L-phenylalanine derivative bearing two hydroxyl substituents on the aromatic ring at the 2- and 6-positions, classifying it as a hydroxy-substituted aromatic amino acid. The molecule contains both a free amino group and a free carboxyl group and features a catechol-like dihydroxy side chain that can participate in hydrogen bonding and redox-active chemistry while remaining consistent with the stereochemical designation implied by "L-" in the name. As a defined amino acid building block, it is used in peptide and amino acid derivative synthesis to introduce a phenylalanine variant with ortho-disubstituted phenolic functionality for structure-activity studies, chemical biology labeling strategies, or preparation of more complex aromatic amino acid conjugates.
CAT No: CP13501
2,6-Dihydroxy-L-Phenylalanine is a hydroxylated phenylalanine derivative featuring two ortho-position phenolic groups on the aromatic side chain, combined with the L-amino acid stereochemistry. This catechol-like motif provides distinct redox and metal-binding behavior compared with unfunctionalized phenylalanine, making it useful when researchers need a reactive, chelating aromatic handle in peptide and materials workflows. As a free amino acid, it also offers the standard amino and carboxyl functionalities for incorporation into synthetic sequences or for further derivatization under controlled conditions.
1. Peptide Building Block Use
2,6-Dihydroxy-L-Phenylalanine is used as a specialized amino acid building block for preparing peptides and peptide analogs that require an ortho-dihydroxy (catechol-like) aromatic side chain. Peptide chemists incorporate this residue into sequence-defined constructs to study aromatic diol-driven interactions, metal coordination effects, or redox-responsive behavior within otherwise conventional peptide backbones. Because the side chain contains two phenolic hydroxyls, it is also selected when downstream functionalization or conjugation depends on maintaining a protected or unprotected phenolic pattern at a defined position in the peptide.
2. Metal Binding And Chelation Studies
2,6-Dihydroxy-L-Phenylalanine supports chemical biology and materials research focused on chelation and coordination chemistry, where catechol-like groups are leveraged to bind metal ions in a controlled, site-specific manner. Researchers use this amino acid to build defined ligands for studying coordination stoichiometry and stability in solution, or to introduce metal-binding motifs into peptide-based scaffolds for adsorption, surface interaction, or controlled assembly. The presence of two ortho hydroxyl groups enables stronger and more directional binding than single-hydroxyl aromatic residues, which is valuable when comparing ligand performance across related amino acid derivatives.
3. Biomaterials And Surface Functionalization
2,6-Dihydroxy-L-Phenylalanine is applied in biomaterials development to introduce dihydroxy aromatic functionality that can promote adhesion or anchoring to metal-containing surfaces and inorganic phases. Materials scientists and polymer researchers often use this amino acid as a reactive precursor to generate coatings, hydrogel components, or surface-tethered ligands where the phenolic groups provide strong interactions with substrates and can be used as a foundation for further chemical modification. In these workflows, the amino acid's bifunctional nature (amino and carboxyl groups plus the dihydroxy side chain) helps integrate the motif into larger macromolecular architectures while preserving the aromatic hydroxyl pattern needed for interfacial performance.
4. Pharmaceutical Intermediate Development
2,6-Dihydroxy-L-Phenylalanine is also used as a research-grade starting material for preparing more complex aromatic amino acid derivatives and heteroatom-functionalized intermediates in medicinal chemistry and specialty chemical manufacturing. Process and development chemists select this scaffold when an ortho-dihydroxy phenylalanine motif is required to enable subsequent derivatization, such as conversion into protected intermediates for library synthesis or transformation into analogs bearing additional functional handles. The defined L-amino acid framework helps maintain stereochemical integrity through downstream steps, supporting the preparation of stereochemically consistent analog series for structure-property studies.
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