3,5-Dihydroxy-D-Phenylalanine is a non-proteinogenic, aromatic amino acid derivative featuring a benzyl side chain substituted with two phenolic hydroxyl groups at the 3- and 5-positions and bearing a free amino group and a free carboxyl group. The molecule is specified in the D configuration at the α-carbon, and the catechol-like phenolic functionality provides hydrogen-bonding and metal-binding behavior while remaining chemically distinct from unmodified phenylalanine. In peptide chemistry and chemical biology, it is employed as a building block for incorporating a redox- and coordination-active aromatic side chain into peptides or for preparing labeled and structure-activity study analogues where phenolic substitution patterns are used to probe binding and reactivity.
CAT No: CP13702
3,5-Dihydroxy-D-Phenylalanine is a D-configured, non-proteinogenic aromatic amino acid featuring two phenolic hydroxyl groups on the meta positions of the benzyl side chain. Its catechol-like functionality makes it a useful building block for chemical biology and materials research where redox-active or phenol-reactive motifs are required, while the D-stereochemistry supports incorporation into non-native peptide architectures and stereochemically defined analogs. Researchers commonly select this scaffold to introduce a rigid, hydroxyl-rich aromatic side chain for downstream conjugation, derivatization, and analytical method development.
1. Peptidomimetic Building Block
3,5-Dihydroxy-D-Phenylalanine is used as an amino acid building block in peptidomimetic and non-natural peptide design, particularly when a D-stereocenter is desired to control stereochemistry and proteolytic stability profiles in synthetic peptide constructs. Medicinal chemistry and chemical biology groups incorporate this residue into short peptide analogs and constrained analog libraries to evaluate how a dihydroxy-substituted aromatic side chain affects physicochemical properties and structure-function relationships. The two phenolic hydroxyl groups provide a chemically addressable handle for further functionalization after peptide assembly, enabling the preparation of site-defined derivatives for binding studies, mechanistic probes, or structure-activity relationship workflows.
2. Phenol-Functionalized Conjugates
3,5-Dihydroxy-D-Phenylalanine is applied in the synthesis of phenol-rich conjugates used for surface immobilization and bioconjugation-oriented materials development. Its catechol-like dihydroxy pattern supports derivatization strategies that attach the aromatic unit to polymers, linkers, or solid supports, allowing researchers to generate defined coatings and reactive interfaces for downstream assays. In chemical biology and biomaterials laboratories, this building block is selected to introduce a hydroxyl-functional aromatic motif that can be used to tune hydrophilicity, enable coupling chemistry, and create stable attachment points in conjugate constructs where aromatic phenolic functionality is a key design element.
3. Redox-Active Materials Chemistry
3,5-Dihydroxy-D-Phenylalanine is leveraged in biomaterials and specialty polymer research where redox-active phenolic groups are valuable for constructing responsive or chemically interactive material surfaces. The dihydroxy-substituted benzyl side chain provides a practical handle for incorporating aromatic hydroxyl functionality into material formulations, coatings, or crosslinkable networks developed for chemical sensing, surface reactivity studies, and materials characterization. Researchers in materials science and industrial R&D use this scaffold to build stereochemically defined components that carry two phenolic hydroxyls, supporting reproducible downstream processing into functional materials platforms.
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