3,5-Dihydroxy-DL-Phenylalanine is a DL (racemic) phenylalanine derivative featuring a benzyl side chain substituted with two hydroxyl groups at the 3- and 5-positions, making it a nonstandard aromatic amino acid. The molecule contains a free α-amino group and a free carboxyl group on the backbone, with the catechol-like dihydroxy functionality contributing phenolic hydrogen-bonding and redox-active behavior under appropriate conditions while the stereocenter is present as a racemate. It is used in peptide and amino acid chemistry as a structurally modified aromatic building block for preparing substituted amino acid derivatives and for studying structure-property relationships involving phenolic side-chain chemistry in solution-phase synthesis and analytical method development.
CAT No: CP13703
3,5-Dihydroxy-DL-Phenylalanine is a catechol-containing phenylalanine derivative featuring two phenolic hydroxyl groups on the aromatic ring, supplied as a DL mixture that supports use where racemic material is acceptable. The presence of a catechol motif makes it a useful building block for chemical derivatization, redox-active labeling strategies, and incorporation into peptide or polymer frameworks when catechol functionality is required. In synthetic and materials workflows, its dihydroxy substitution pattern is leveraged to introduce strong metal-binding and surface-adhesion-like chemistry, as well as to enable downstream conjugation and analytical derivatization.
1. Catechol-Functionalized Peptide Building
3,5-Dihydroxy-DL-Phenylalanine is used as a catechol-bearing amino acid building block for preparing modified peptides and peptidomimetics where aromatic dihydroxy functionality is needed for chemical handle introduction. Researchers in peptide chemistry and chemical biology employ it to introduce a redox-active, metal-coordinating side chain into peptide sequences for structure-property studies, surface-binding assays, and coordination-driven assembly experiments. The DL stereochemical mixture is often selected for exploratory studies focused on catechol reactivity and derivatization rather than strict stereochemical control.
2. Metal Coordination Materials And Coatings
3,5-Dihydroxy-DL-Phenylalanine is commonly used in biomaterials and surface chemistry development to impart catechol-type binding behavior to polymers, coatings, and material precursors. Materials scientists incorporate this amino acid derivative into synthetic architectures to promote strong interactions with metal ions and to support metal-mediated crosslinking or surface immobilization workflows. The two phenolic hydroxyl groups provide the key coordination functionality that downstream formulations can exploit for adhesion-like performance on inorganic substrates and for constructing coordination-stabilized networks.
3. Chemical Biology Derivatization Reagents
3,5-Dihydroxy-DL-Phenylalanine serves as a catechol-functional substrate for chemical biology workflows that require phenolic hydroxyl groups as reactive sites for derivatization. In practice, it is used to generate labeled or functionalized intermediates for conjugation strategies, including catechol-based coupling approaches to surfaces or biomolecule scaffolds where dihydroxy substitution is the defining feature. Analytical and research groups also use it as a reference catechol-containing amino acid derivative for method development that depends on catechol-specific derivatization chemistry.
4. Analytical Standards For Catechol Chemistry
3,5-Dihydroxy-DL-Phenylalanine is used to support analytical method development and quality control in studies involving catechol-containing compounds and amino acid derivatives. Laboratories use it as a chemical standard to calibrate detection workflows that rely on catechol reactivity and characteristic derivatization behavior, including LC-based quantification and derivatization-assisted detection schemes. The racemic DL supply is often acceptable for analytical calibration when the method response is governed primarily by the catechol functional group rather than stereospecific separation.
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5. SERS spectrum of the peptide thymosin‐β4 obtained with Ag nanorod substrate
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