2,4-Dihydroxy-DL-Phenylalanine is a substituted phenylalanine derivative classified as a natural-amino-acid analog, featuring a benzene ring bearing hydroxyl substituents at the 2- and 4-positions relative to the side-chain attachment. The molecule contains both an amino group and a carboxyl group on the α-carbon and is specified as DL, indicating a racemic mixture of stereoisomers at the chiral center, with side-chain phenolic hydroxyl functionality that can participate in hydrogen bonding and acid-base behavior typical of phenols. As a free amino acid analog, it is used in peptide and structure-activity study contexts as a building block to introduce a dihydroxyphenyl side chain for probing aromatic hydroxyl effects, as well as in analytical method development where phenolic amino-acid standards or derivatization targets are required.
CAT No: CP13303
2,4-Dihydroxy-DL-Phenylalanine is a racemic (DL) phenylalanine derivative bearing two phenolic hydroxyl groups at the 2- and 4-positions on the aromatic ring. This catechol-like substitution pattern makes it a useful aromatic amino acid building block for medicinal chemistry and chemical biology workflows where redox-active or metal-interacting phenols are valuable. As a free amino acid, it provides both an amino functionality and a carboxylic acid for incorporation into synthetic sequences, while the dihydroxy motif supports derivatization and downstream conjugation chemistry.
1. Medicinal Chemistry Building Block
2,4-Dihydroxy-DL-Phenylalanine is used as an aromatic amino acid scaffold in small-molecule and peptidomimetic discovery programs, particularly when a dihydroxy-substituted phenylalanine motif is needed to probe structure-activity relationships. Medicinal chemistry groups employ this building block to introduce phenolic functionality that can participate in hydrogen bonding networks and enable redox/metal-coordination behavior in target-binding studies, while retaining the amino acid backbone handle for further functionalization. Its DL stereochemical form is commonly selected in early-stage SAR synthesis where racemate tolerance simplifies library preparation and rapid analog generation.
2. Peptidomimetic And Peptide Analog Synthesis
2,4-Dihydroxy-DL-Phenylalanine serves as a practical precursor for peptide analogs and constrained peptidomimetic structures that incorporate a dihydroxy-substituted aromatic side chain. Researchers in peptide chemistry and chemical biology use it to generate analogs for studying how aromatic hydroxyl patterning affects conformation, intermolecular interactions, and recognition by enzymes or binding partners in vitro. The presence of both the amino and carboxyl groups supports its use as an amino acid building block in downstream coupling strategies, while the 2,4-dihydroxy substitution provides a chemically distinctive side-chain environment for designing structure-function experiments.
3. Bioconjugation And Surface Functionalization
2,4-Dihydroxy-DL-Phenylalanine is frequently incorporated into conjugation and immobilization workflows where phenolic groups are leveraged for attachment strategies to polymers, linkers, or surfaces. Chemical biology and biomaterials teams use this scaffold to introduce dihydroxy functionality into custom conjugates, enabling subsequent derivatization steps that rely on phenol reactivity or metal-mediated binding approaches. The amino acid backbone also provides a convenient starting point for preparing defined conjugate architectures, including linkers used to present aromatic hydroxyl motifs in multicomponent materials and assay reagents.
4. Analytical Reference For Derivative Studies
2,4-Dihydroxy-DL-Phenylalanine is used as a reference material in analytical method development and characterization of dihydroxy-phenylalanine-containing derivatives. Analytical chemists and metabolomics-focused laboratories employ it to support LC-MS or related workflows when confirming the identity of hydroxylated phenylalanine analogs, monitoring derivatization efficiency, or validating chromatographic behavior of structurally related compounds. The racemic DL form is particularly useful for comparative studies where retention time and mass spectral features of the dihydroxy substitution pattern are the primary analytical targets rather than stereospecific separation.
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