3-Hydroxy-D-Phenylalanine is a non-proteinogenic, hydroxylated amino acid derivative featuring a D-configured α-amino acid backbone with a benzyl side chain bearing a phenolic 3-hydroxy substituent. The molecule contains a free amino group and a carboxyl group, and the additional phenolic hydroxyl provides hydrogen-bonding and acid-base behavior that can influence conformational preferences and side-chain reactivity during peptide coupling. It is used in peptide chemistry and chemical biology for introducing a polar aromatic hydroxyl handle into structure-activity studies, enabling controlled incorporation of a modified aromatic residue and supporting analytical method development for labeled or hydroxyl-functionalized amino acid derivatives.
CAT No: CP14802
CAS No:32140-49-1
Synonyms/Alias:D-m-Tyrosine;32140-49-1;3-Hydroxy-D-phenylalanine;L-3-hydroxyphenylalanine;(2R)-2-amino-3-(3-hydroxyphenyl)propanoicacid;(R)-2-AMINO-3-(3-HYDROXYPHENYL)PROPANOICACID;D-META-TYROSINE;AC1OCTY4;H-D-META-TYR-OH;m-hydroxy-D-phenylalanine;(R)-M-TYROSINE;D-M-TYR-OH;D-PHE(3-OH)-OH;H-D-PHE(3-OH)-OH;SCHEMBL4356402;MolPort-003-794-809;ZINC392007;ACT02392;RW2352;AB15920;AM83355;AJ-21204;AK-44642;BC227225;BR-44642
3-Hydroxy-D-Phenylalanine is a D-configured, non-proteinogenic aromatic amino acid featuring a side-chain phenolic hydroxyl group that enables selective derivatization and strong participation in peptide and peptidomimetic structure-property studies. Its stereochemistry and phenolic functionality make it a useful building block for incorporating a defined chiral, hydrogen-bonding motif into synthetic peptides and medicinal chemistry scaffolds, including analogs designed to probe aromatic hydroxyl effects on conformation and reactivity. In research settings, it is also used as a chemically defined reference material for analytical workflows that distinguish hydroxylated phenylalanine variants.
1. Peptidomimetic Building Block
3-Hydroxy-D-Phenylalanine is used by peptide chemistry and medicinal chemistry teams to prepare peptidomimetic sequences and constrained analogs where a D-amino acid and a phenolic hydroxyl side chain are required to tune local stereochemistry, hydrogen-bonding capacity, and aromatic presentation. The defined D-configuration supports studies that compare stereochemical outcomes in structure-activity relationship (SAR) campaigns, while the phenolic hydroxyl provides a handle for downstream functionalization or controlled protection strategies during fragment assembly. Typical downstream products include modified peptide leads, inhibitor analogs, and synthetic standards used to benchmark hydroxylated aromatic residue incorporation in custom peptide synthesis.
2. Medicinal Chemistry SAR Probes
3-Hydroxy-D-Phenylalanine supports medicinal chemistry programs that evaluate how an aromatic hydroxyl substituent and D-stereochemistry influence physicochemical behavior and chemical reactivity within lead optimization series. Researchers commonly incorporate this residue into small peptide-like scaffolds to generate analog panels for SAR testing, where the phenolic group can be leveraged for selective derivatization during characterization and impurity profiling. Because the compound is a single, well-defined amino acid building block rather than a mixture, it is also used to prepare reference materials for comparing hydroxylated phenylalanine-containing compounds across synthesis batches and analytical methods.
3. Analytical Reference Derivatization
3-Hydroxy-D-Phenylalanine is frequently used in analytical chemistry workflows that require a chemically defined hydroxylated phenylalanine standard for method development and quality control of amino acid-related measurements. The phenolic hydroxyl enables derivatization strategies that improve detectability or chromatographic behavior when separating hydroxylated aromatic amino acid species, and the D-configuration helps distinguish stereoisomeric variants when chiral separation or stereospecific derivatization is part of the method. Laboratories use this compound to validate retention behavior, calibrate quantitation for hydroxylated phenylalanine standards, and support identification of hydroxylated aromatic residues in complex sample matrices such as hydrolysates from peptide or protein studies.
4. Chemical Biology Substrate Analogues
3-Hydroxy-D-Phenylalanine is used by chemical biology groups to generate substrate analogues and residue-specific probes for studying enzyme selectivity toward hydroxylated aromatic amino acid motifs in synthetic systems. Its phenolic hydroxyl group provides a functional feature that can be monitored directly or converted into reporter derivatives for downstream readouts, while the D-stereochemistry helps probe stereochemical preferences in controlled assay formats. In practice, it is incorporated into short synthetic peptides or used as a defined component in reagent sets where the goal is to compare reactivity patterns of hydroxylated phenylalanine residues under standardized experimental conditions.
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