3,4-Dihydroxy-L-Phenylalanine is a naturally occurring, proteinogenic amino acid derivative in which the phenylalanine side chain bears two adjacent hydroxyl groups at the 3 and 4 positions, forming a catechol functionality on the aromatic ring. The molecule contains both an amino group and a carboxyl group, with the stereocenter corresponding to the L-configuration indicated in the name, and the catechol side chain can participate in hydrogen bonding and redox-active chemistry typical of dihydroxyphenyl motifs. It is used as a defined building block for peptide and protein-analog synthesis and for chemical studies that probe how catechol-bearing side chains influence structure, conjugation chemistry, and analytical behavior.
CAT No: CP13601
CAS No:59-92-7
Synonyms/Alias:N-acetyl-D-proline;59785-68-1;1-ACETYL-D-PROLINE;(R)-1-Acetylpyrrolidine-2-carboxylicacid;AC-D-PRO-OH;D-Proline,1-acetyl-;N-Acetylproline;(2R)-1-acetylpyrrolidine-2-carboxylicacid;CHEBI:44272;(R)-(+)-Acetylproline;4ayu;AmbotzAAA1931;Ac-D-Prn-OH;AC1LEX4B;SCHEMBL428477;CHEMBL3137742;CTK1G9158;GNMSLDIYJOSUSW-ZCFIWIBFSA-N;MolPort-003-983-009;ZINC119667;ANW-41538;CA-577;AKOS015841039;AM82194;DB03360
3,4-Dihydroxy-L-Phenylalanine is a catechol-bearing L-amino acid featuring two phenolic hydroxyl groups on the aromatic ring, enabling redox-active and metal-coordinating chemistry alongside the standard amino acid functionality. This structure is frequently leveraged in chemical biology and materials research where catechol-mediated adhesion, surface binding, and oxidative coupling are advantageous. In peptide and protein contexts, it serves as a chemically defined building block for introducing a catechol motif that can be used to tune reactivity and binding behavior in downstream conjugation workflows.
1. Catechol Surface Functionalization
3,4-Dihydroxy-L-Phenylalanine is used to build catechol-rich coatings and surface coatings for biomaterials and materials interfaces, where the catechol groups promote strong anchoring to metal oxides and other reactive surfaces. Researchers in biomaterials development and surface chemistry use it to prepare functional layers that support subsequent immobilization of biomolecules or polymers, taking advantage of the amino acid's well-defined structure rather than relying on heterogeneous catechol mixtures. The presence of two phenolic hydroxyls supports robust interfacial chemistry for creating stable, chemically addressable material surfaces used in cell-interaction studies, biosensor interfaces, and polymer conjugation strategies.
2. Peptide Conjugation Building Block
3,4-Dihydroxy-L-Phenylalanine is applied as a defined amino acid building block to incorporate catechol functionality into peptides and peptide-based linkers used in chemical biology workflows. Custom peptide synthesis teams and academic groups use it to introduce a reactive aromatic motif that can participate in site-specific coupling and surface immobilization steps during probe or affinity reagent preparation. Because the catechol is part of the side chain, it offers a controllable handle for downstream conjugation workflows where a catechol group is required to drive attachment to surfaces or to enable oxidative crosslinking in material and bioconjugate assembly pipelines.
3. Bioorthogonal Catechol Chemistry
3,4-Dihydroxy-L-Phenylalanine is frequently selected for chemical biology experiments that require catechol-mediated reactivity as a tool for labeling, immobilization, and controlled assembly of biomolecular constructs. Chemical biology laboratories use it to generate catechol-functional intermediates that can be coupled into larger systems such as affinity reagents, immobilized enzymes, or multicomponent biomolecular assemblies where catechol chemistry provides a practical route to stable association. The defined L-configuration and catechol side chain support reproducible performance in workflows that depend on catechol-driven interactions rather than relying on less controlled catechol-containing reagents.
4. Analytical Reference and Standards
3,4-Dihydroxy-L-Phenylalanine is used as a reference material for analytical method development and quantitation in studies involving catechol-containing amino acid species. Analytical chemistry groups and metabolomics laboratories employ it to support calibration strategies, retention-time verification, and identity confirmation in LC-based workflows where catechol-bearing analytes are monitored. The well-characterized structure and amino acid identity make it useful for preparing analytical standards and for validating sample processing approaches in studies that track catechol amino acid derivatives or related aromatic hydroxylated compounds.
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