2-Hydroxy-D-Phenylalanine is a non-proteinogenic amino acid derivative featuring a phenylalanine backbone bearing an additional hydroxyl substituent at the 2-position of the side chain and a D-stereochemical configuration as indicated by the name. The molecule contains a free amino group and a free carboxyl group, allowing it to exist as a zwitterion in solution, while the side-chain hydroxyl provides hydrogen-bonding and polarity that can influence incorporation behavior in peptide-forming reactions. In chemical biology and peptide chemistry workflows, it is used as a substrate analogue or building block for preparing modified peptides and structure-activity studies where an extra hydroxyl functionality on a phenylalanine-like scaffold is required.
CAT No: CP14702
CAS No:24008-77-3
Synonyms/Alias:2-Hydroxy-D-Phenylalanine;24008-77-3;(R)-2-Amino-3-(2-hydroxyphenyl)propanoicacid;(+)-o-Tyrosine;D-o-Tyrosine;D-o-Hydroxyphenylalanine;D-PHE(2-OH)-OH;(2R)-2-amino-3-(2-hydroxyphenyl)propanoicacid;AC1OCTXS;D-Phenylalanine,2-hydroxy-;D-2-HYDROXYPHENYLALANINE;SCHEMBL13537520;CTK4F2747;MolPort-005-943-592;ZINC392005;1711AB;ANW-63263;CH-421;AB21388;AM83352;AJ-21202;AK-87829;KB-24527;DB-021205;TC-152008
2-Hydroxy-D-Phenylalanine is a D-configured hydroxy-substituted phenylalanine derivative featuring a benzylic secondary alcohol on the side chain. This stereochemically defined amino acid is frequently used as a chiral building block for peptide and peptidomimetic construction, as well as for stereochemical studies where D-amino acid identity is essential. The presence of the hydroxyl functionality also makes it a practical precursor for downstream derivatization and analytical method development requiring a defined aromatic alcohol motif.
1. Peptidomimetic Building Block
2-Hydroxy-D-Phenylalanine is used by medicinal chemistry and peptide research groups to introduce a D-configured aromatic hydroxyl motif into peptidomimetics and constrained analogs. Researchers commonly incorporate this building block into solution-phase or solid-phase peptide assembly workflows when a benzylic secondary alcohol is needed for side-chain stereochemical control, hydrogen-bonding interactions, or to emulate hydroxyl-bearing pharmacophores in structure-activity relationship studies. Its defined D-stereochemistry supports the preparation of stereochemically pure analog series for SAR and conformational comparisons, where switching between L- and D-configured amino acid analogs can materially change physicochemical behavior.
2. Chiral Intermediate For Synthesis
2-Hydroxy-D-Phenylalanine serves as a chiral intermediate in pharmaceutical intermediate development and specialty chemical manufacturing where a D-amino acid scaffold bearing an aromatic secondary alcohol is required. Process and R&D chemists use it to access downstream stereodefined intermediates for heterocycle formation, protected alcohol transformations, and the preparation of hydroxylated aromatic side-chain fragments used in larger synthetic sequences. The combination of an amino acid backbone and a reactive hydroxyl group enables targeted functionalization steps that preserve stereochemical integrity, supporting the development of defined stereoisomer libraries and custom intermediates for lead optimization programs.
3. Analytical Reference And Derivatization
2-Hydroxy-D-Phenylalanine is also used in analytical chemistry workflows as a defined stereochemical reference material and derivatization substrate for quantification and method validation. Laboratories preparing LC-MS or chiral chromatography methods for hydroxylated amino acid species rely on D-configured standards to confirm retention behavior and mass spectral signatures for benzylic alcohol-containing phenylalanine derivatives. In addition, the secondary alcohol functionality supports derivatization strategies that improve chromatographic properties or detector response for amino acid profiling, enabling more reliable comparison between stereoisomeric analytes in research-grade assays.
4. Stereochemical Control In SAR
2-Hydroxy-D-Phenylalanine is frequently selected by structure-activity relationship teams to systematically vary stereochemistry at the amino acid center while maintaining an aromatic hydroxyl side chain. In medicinal chemistry programs, this enables focused evaluation of how D-configuration and the presence of a secondary alcohol influence binding-relevant features such as hydrogen-bonding patterns and local polarity across analog series. Because the molecule is a single, well-defined stereoisomeric building block, it is particularly useful for generating consistent analog sets for structure-property studies, where minimizing ambiguity in stereochemical identity improves interpretability of downstream data.
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