2-Hydroxy-DL-Phenylalanine is a hydroxy-substituted phenylalanine derivative featuring a benzyl side chain bearing a hydroxyl group, classed as an amino acid analogue with both amino and carboxyl functional groups. The molecule is provided as a DL (racemic) mixture, so it contains both stereochemical forms at the α-carbon, and the side-chain hydroxyl introduces an additional hydrogen-bonding and polarity element that can influence conformational preferences and intermolecular interactions. In peptide and chemical biology workflows, this compound is used as a substrate-like building block to introduce a hydroxylated aromatic side chain into peptide structures for structure-activity studies, conjugation handle design, and analytical method development involving amino acid derivative standards.
CAT No: CP14703
CAS No:2370-61-8
Synonyms/Alias:DL-o-Tyrosine;2370-61-8;2-amino-3-(2-hydroxyphenyl)propanoicacid;O-Tyrosine;2-Hydroxyphenylalanine;2-hydroxy-DL-Phenylalanine;Ortho-tyrosine;2-Tyrosine;o-Tyrosine,DL-;DL-3-(o-Hydroxyphenyl)alanine;2-Amino-3-(2-hydroxyphenyl)propionicAcid;DL-2-TYROSINE;Alanine,3-(o-hydroxyphenyl)-,DL;3-(2-Hydroxyphenyl)-DL-alanine;EINECS219-134-8;NSC72345;ST50407955;(+/-)-2-Amino-3-(2-hydroxyphenyl)propionicacid;Phenylalanine,2-hydroxy-;709-16-0;DL-3-(2-HYDROXYPHENYL)ALANINE;o-DL-Tyrosine;D,L-o-Tyrosine;(+/-)-o-Tyrosine;2-hydroxy-Phenylalanine
2-Hydroxy-DL-Phenylalanine is a DL mixture of 2-hydroxy-substituted phenylalanine, featuring a benzylic secondary alcohol alongside the amino acid functional group. This stereochemically mixed, hydroxyl-bearing amino acid is commonly used as a structural building block in medicinal chemistry and peptide/peptidomimetic research where side-chain hydroxyl functionality is required for hydrogen bonding, conformational effects, or derivatization. Its presence in both enantiomeric forms supports method development and intermediate synthesis workflows that do not require strict stereochemical purity.
1. Peptidomimetic Building Blocks
2-Hydroxy-DL-Phenylalanine is used as a hydroxyl-functional amino acid building block for constructing peptidomimetics and constrained analogs in chemical biology and medicinal chemistry programs. Researchers incorporate the 2-hydroxy side chain to introduce additional hydrogen-bonding interactions and to modulate local geometry relative to unfunctionalized phenylalanine derivatives. The DL form is frequently selected for early-stage library synthesis, SAR exploration, and comparative studies where both stereochemical variants are acceptable for downstream screening or for generating reference material sets.
2. Medicinal Chemistry Intermediates
2-Hydroxy-DL-Phenylalanine serves as a practical intermediate for preparing substituted aromatic amino acid derivatives used in medicinal chemistry route development. The secondary alcohol enables straightforward functional diversification into protected alcohols, ester/ether derivatives, or handle-bearing intermediates that can be carried into subsequent coupling, cyclization, or conjugation steps. Pharmaceutical intermediate development teams often choose this DL material when the stereochemical outcome is not yet fixed, when rapid access to analog series is prioritized, or when the hydroxyl group is a key functional element for tuning physicochemical properties in analog design.
3. Chiral Derivative Screening
2-Hydroxy-DL-Phenylalanine is also used in workflows that generate and evaluate stereochemical variants, including the preparation of chiral derivatives for separation, characterization, or downstream resolution strategies. Because the starting material contains both enantiomers, it is well suited to comparative analytical studies such as method development for chiral HPLC/UPLC, derivatization optimization, and establishing chromatographic behavior of hydroxyl-substituted phenylalanine analogs. Analytical and process development groups commonly use this form to build reference panels and to support decision-making on whether enantiopure material is required for later-stage synthesis.
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