2,6-Dihydroxy-DL-Phenylalanine is a DL (racemic) phenylalanine derivative bearing two hydroxyl substituents on the aromatic ring at the 2- and 6-positions, classifying it as a non-proteinogenic, ring-functionalized amino acid. The molecule contains a free amino group and a free carboxyl group alongside a benzyl side chain substituted with catechol-like dihydroxy functionality, and its stereochemistry is specified only as DL, indicating an equal mixture of enantiomers at the α-carbon. As an aromatic, hydroxyl-bearing amino acid analogue, it is used in peptide and amino acid derivative synthesis to introduce phenyl ring hydroxyl functionality for structure-activity studies, protein engineering experiments, and analytical method development where defined catechol-like substitution patterns are required.
CAT No: CP13503
2,6-Dihydroxy-DL-Phenylalanine is a DL-form aromatic amino acid featuring two phenolic hydroxyl groups at the 2- and 6-positions on the benzyl side chain, alongside the standard amino and carboxylic acid functionality. This catechol-like substitution pattern makes it a useful building block for chemists seeking ortho-disubstituted phenol chemistry, including controlled reactivity in peptide and small-molecule synthesis. Its DL stereochemistry supports broad synthetic flexibility for structure-property studies and intermediate preparation where enantiopure material is not required.
1. Phenolic Building Block Synthesis
2,6-Dihydroxy-DL-Phenylalanine is used as an aromatic amino acid building block in the preparation of catechol-functionalized intermediates for medicinal chemistry and peptidomimetic development. The closely positioned 2,6-dihydroxy substitution pattern provides a defined phenolic handle for downstream derivatization into protected phenol derivatives, ester or ether linkages, or conjugation-ready motifs. Research groups developing small-molecule ligands, polymerizable monomers, or bio-inspired catechol analogs often select this amino acid precursor because it combines a reactive phenolic motif with an amino acid backbone that can be carried through multi-step syntheses without losing the key side-chain functionality.
2. Peptide And Peptidomimetic Incorporation
2,6-Dihydroxy-DL-Phenylalanine is commonly employed in peptide synthesis and peptidomimetic assembly workflows where a sterically shielded, ortho-disubstituted phenol side chain is required for structure-activity relationship studies. The two phenolic hydroxyl groups enable incorporation of catechol-like chemistry into peptide scaffolds, supporting the preparation of analog libraries used to probe how side-chain electronics and steric environment influence binding, conformation, or chemical reactivity. Because the product is provided as a DL mixture, it is frequently chosen for exploratory library synthesis and intermediate generation where relative stereochemistry is not the primary variable, while still delivering the distinctive 2,6-dihydroxy phenylalanine side chain.
3. Crosslinking And Surface Functionalization Precursors
2,6-Dihydroxy-DL-Phenylalanine serves as a precursor for catechol-enabled crosslinking and surface functionalization strategies in biomaterials and chemical biology tool development. The 2,6-dihydroxy pattern provides phenolic groups that can be converted into reactive derivatives for attaching to polymers, nanoparticles, or biomaterial surfaces, enabling catechol-based coupling chemistry in downstream materials processing. Materials researchers and industrial R&D teams often use this amino acid to introduce a defined catechol motif into custom linkers or to generate amino acid-derived monomers that can be incorporated into coatings, hydrogels, or functional polymer networks, where the side-chain hydroxyl functionality is the key design element.
4. Analytical Reference For Catechol Amino Acid Chemistry
2,6-Dihydroxy-DL-Phenylalanine is used as a reference material and chemical standard in analytical method development targeting catechol-containing amino acid motifs. Laboratories developing LC-MS workflows for aromatic dihydroxy amino acids, or validating sample preparation steps for phenolic amino acid derivatives, rely on this compound to benchmark retention behavior and to establish calibration or qualifier signals for the target functional group pattern. In research settings focused on chemical stability, derivatization efficiency, or quantitation of phenolic species, the defined 2,6-dihydroxy substitution pattern makes it a practical standard for verifying that analytical procedures capture catechol-like amino acid chemistry consistently.
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