2,5-Dihydroxy-L-Phenylalanine is a naturally occurring, proteinogenic amino acid derivative in which the phenylalanine side chain bears two hydroxyl substituents at the 2- and 5-positions of the aromatic ring. The molecule contains a free α-amino group and a free α-carboxyl group with an L-stereochemical configuration as indicated by the name, while the catechol-like dihydroxy functionality on the benzyl side chain provides phenolic hydrogen-bonding and redox-active behavior typical of ortho- and para-substituted diols. In peptide and biochemical research, it is used as a chemically defined building block for incorporating a dihydroxyphenylalanine residue into synthetic peptides and for structure-function or labeling studies where aromatic hydroxyl groups are required for conjugation, crosslinking chemistry, or analytical differentiation.
CAT No: CP13401
2,5-Dihydroxy-L-Phenylalanine is a hydroxylated L-phenylalanine derivative bearing two phenolic groups on the aromatic side chain, which makes it a chemically distinctive building block for catechol-like reactivity and controlled functionalization. Its free amino acid functionality supports incorporation into peptide and polymer architectures, while the dihydroxy substitution pattern enables downstream derivatization for analytical and materials workflows. Researchers select this compound when a phenolic, redox-active, or metal-binding motif is required without introducing a larger aromatic substituent.
1. Peptide And Conjugate Building
2,5-Dihydroxy-L-Phenylalanine is used as a functional amino acid building block for preparing peptides and peptide-like conjugates that incorporate a dihydroxyphenyl side chain for site-specific chemical functionality. In custom peptide synthesis and structure-property studies, the compound enables placement of a catechol-like motif at a defined position to support subsequent derivatization steps used in chemical biology tool development and materials-oriented peptide design. Because the side chain contains two phenolic hydroxyls, it is often selected when downstream coupling chemistry or metal coordination behavior is needed directly from the amino acid side chain rather than from an added linker.
2. Analytical Standards For Phenolic Amino Acids
2,5-Dihydroxy-L-Phenylalanine is commonly used to support analytical method development and quantitation workflows targeting hydroxylated phenylalanine species in complex matrices. Analytical chemists employ it as a reference material for LC-MS and related platforms where a structurally matched standard improves identification confidence for dihydroxyphenylalanine-related peaks and supports calibration strategies. The presence of two phenolic groups provides a distinctive chemical signature compared with mono-hydroxylated analogs, making it useful when differentiating closely related aromatic amino acid derivatives in metabolite profiling or targeted compositional studies.
3. Biomaterials Surface Functionalization
2,5-Dihydroxy-L-Phenylalanine is applied in biomaterials research where catechol-like phenolic functionality is leveraged to promote surface attachment and interfacial modification. Materials scientists use it as a reactive amino acid component in the construction of coatings, hydrogel formulations, and polymer conjugates that require strong interfacial interactions or metal-mediated assembly strategies. The dihydroxy substitution pattern supports practical downstream functionalization routes for creating materials with defined aromatic hydroxyl density, enabling reproducible surface chemistry in research-grade biomaterial development.
4. Metal Coordination And Linker Design
2,5-Dihydroxy-L-Phenylalanine is used as a ligand-bearing amino acid building block for designing metal-coordination motifs in chemical biology and materials chemistry workflows. Researchers incorporate the dihydroxyphenyl side chain into intermediate constructs to enable controlled binding to metal ions or to tune coordination environments for subsequent assembly steps. This makes the compound particularly relevant when a bidentate phenolic motif is desired as part of an amino acid-derived linker, rather than relying on separate small-molecule ligands that may complicate downstream characterization or stoichiometry.
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