3,5-Dihydroxy-L-Phenylalanine is an L-phenylalanine-derived amino acid bearing a phenyl ring substituted with hydroxyl groups at the 3 and 5 positions, classifying it as a natural-proteinogenic backbone analogue with catechol-like substitution. The molecule contains a free amino group and a free carboxyl group alongside two phenolic hydroxyl functionalities, and the L-configuration indicated in the name specifies the stereochemical form at the α-carbon. As a chemically functionalized aromatic amino acid, it is used in peptide synthesis and structure-activity or protein-analogue studies where the additional phenolic groups provide handles for conjugation, metal coordination, or controlled redox/derivatization chemistry under appropriate conditions.
CAT No: CP13701
3,5-Dihydroxy-L-Phenylalanine is a hydroxylated L-phenylalanine derivative bearing two phenolic hydroxyl groups on the aromatic ring, making it a useful catechol-like amino acid building block for chemical synthesis and analytical reference work. Its strongly hydrogen-bonding, redox-active phenolic functionality supports downstream derivatization and incorporation into aromatic peptide or small-molecule frameworks where controlled phenol chemistry is required. Researchers commonly select this compound when a defined dihydroxy substitution pattern on an amino acid scaffold is needed for structure-property studies, derivatization strategies, or mass spectrometry standardization.
1. Phenolic Building Block Synthesis
3,5-Dihydroxy-L-Phenylalanine is used as a defined aromatic amino acid building block for constructing phenol-rich peptides, peptidomimetics, and small-molecule scaffolds in medicinal chemistry and chemical biology research. The two ortho-positioned hydroxyl groups provide a predictable handle for further functionalization, enabling the development of analog series that probe how catechol-like substitution patterns influence reactivity, conjugation efficiency, and physicochemical behavior. Synthetic teams often rely on this specific substitution pattern to ensure that downstream coupling, derivatization, or analytical readouts reflect the intended dihydroxy arrangement rather than a mono-hydroxyl or differently substituted phenylalanine analog.
2. Peptide And Conjugate Derivatization
3,5-Dihydroxy-L-Phenylalanine supports workflows where phenolic amino acid residues are required for post-synthetic modification or for preparing conjugation-ready intermediates. In custom peptide and bioconjugation development, the catechol-like functionality can be leveraged to generate defined derivatives that are compatible with downstream coupling chemistries used to assemble aromatic peptide conjugates, surface-immobilized linkers, or functionalized biomolecule adducts. Teams in biomaterials and chemical biology frequently choose this scaffold when they need a stable, well-characterized amino acid core that carries two reactive phenolic sites for controlled derivatization planning.
3. LC-MS And NMR Analytical Standards
3,5-Dihydroxy-L-Phenylalanine is widely used as an analytical reference material for method development and quantitation in LC-MS workflows that monitor hydroxylated aromatic amino acid motifs. The presence of two phenolic hydroxyl groups yields characteristic chemical behavior that helps laboratories validate extraction, derivatization, and detection conditions for dihydroxy-substituted phenylalanine species. Analytical chemistry groups also use this compound as a structural benchmark for NMR and chromatographic characterization when confirming the identity and purity of hydroxylated amino acid derivatives, peptide fragments, or reaction mixtures where catechol-like substitution must be verified.
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