2,4-Dihydroxy-D-Phenylalanine is a D-configured, non-proteinogenic amino acid characterized by a phenylalanine backbone bearing two hydroxyl substituents at the 2- and 4-positions of the aromatic ring. The molecule contains a free amino group and a carboxyl group and features an additional catechol-like dihydroxy functionality that can participate in hydrogen bonding and redox-dependent chemistry typical of phenolic groups. As an amino acid building block for peptide and peptidomimetic synthesis, it provides a defined aromatic dihydroxy side chain for structure-activity studies, conjugation handle formation, and analytical method development involving chemically characterized aromatic hydroxyl patterns.
CAT No: CP13302
2,4-Dihydroxy-D-Phenylalanine is a D-configured phenylalanine derivative bearing two phenolic hydroxyl groups at the 2- and 4-positions on the aromatic ring. This catechol-like substitution pattern provides a distinct redox- and chelation-relevant side-chain functionality while maintaining the amino acid backbone required for peptide and materials chemistry workflows. Researchers use this building block to introduce a stereochemically defined, dihydroxy-phenyl side chain into synthetic sequences and to support analytical or biomimetic studies where aromatic hydroxyl functionality is a key design element.
1. Peptide Building Block Use
2,4-Dihydroxy-D-Phenylalanine is used as a stereodefined amino acid building block for incorporating dihydroxy-phenyl side chains into synthetic peptides and peptide mimetics. Its D-configuration supports workflows aiming to control backbone stereochemistry and to probe how non-proteinogenic stereochemical features influence peptide conformation and stability in chemical biology studies. The aromatic diol functionality also enables downstream derivatization strategies used in peptide library construction, including selective functional transformations of phenolic groups for conjugation, surface attachment, or assay-compatible labeling.
2. Bioconjugation And Surface Chemistry
2,4-Dihydroxy-D-Phenylalanine is applied in bioconjugation and biomaterials surface-functionalization programs where phenolic hydroxyl groups provide reactive handles for post-coupling modification. Teams developing peptide-based linkers, coating layers, or immobilized biomolecules often select this building block to introduce a defined dihydroxy-aryl motif that can be carried through to the final conjugate architecture. In such workflows, the amino acid backbone supports incorporation into larger constructs, while the 2,4-dihydroxy substitution pattern supports subsequent chemical tailoring for immobilization chemistry and material interface engineering.
3. Analytical Standard And Assay Reagents
2,4-Dihydroxy-D-Phenylalanine is also used to prepare analytical standards and reference materials for method development in LC-based quantification and characterization of catechol-like aromatic amino acid derivatives. Analytical groups use it to validate retention behavior, fragmentation patterns, and derivatization performance when monitoring dihydroxy-phenylalanine species in complex matrices such as reaction mixtures, polymer-bound samples, or specialty chemical intermediates. The defined D-stereochemistry and the presence of two phenolic hydroxyl groups make it particularly useful when distinguishing stereochemical or substitution-pattern variants during analytical method qualification.
4. Biomimetic Material Functionalization
2,4-Dihydroxy-D-Phenylalanine supports biomimetic and functional polymer design efforts that require aromatic dihydroxyl functionality to tune surface interactions and chemical reactivity. Materials scientists incorporate this amino acid derivative into peptide-based polymers, crosslinkable linkers, or coating-forming segments to introduce a defined dihydroxy-aryl motif at controlled positions within the macromolecular framework. The resulting functional materials are then used in research settings focused on interface chemistry, coating stability, and chemically addressable surface modification routes where phenolic hydroxyl groups are a central design feature.
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