(RS)-2-Hydroxy-3-(3-pyridyl)-propionic acid is a non-proteinogenic, aromatic amino acid derivative featuring a three-carbon propionic acid backbone with a hydroxyl substituent at C2 and a 3-pyridyl side chain at C3. The molecule contains both a carboxylic acid and a hydroxyl-bearing stereogenic center within an (RS) stereochemical mixture, and the pyridine ring provides a basic nitrogen that can participate in acid-base equilibria and coordination chemistry while the side-chain hydroxyl can act as a hydrogen-bond donor/acceptor. As a chemically defined building block, it is used in peptide and small-molecule synthesis to introduce a pyridyl functionality for structure-activity studies, receptor-binding motif exploration, and analytical method development, including the preparation of conjugates and heteroaromatic-containing derivatives.
CAT No: CP27567
CAS No:889957-22-6
Synonyms/Alias:889957-22-6;(RS)-2-HYDROXY-3-(3-PYRIDYL)-PROPIONICACID;(RS)-2-HYDROXY-3-(PYRIDIN-3-YL)-PROPANOICACID;SCHEMBL1827062;CTK5G2148;4393AH;AKOS006276076;DA-01740;HE275993;2-hydroxy-3-(pyridin-3-yl)propanoicacid
(RS)-2-Hydroxy-3-(3-pyridyl)-propionic acid is a racemic hydroxy-substituted amino acid analog bearing a 3-pyridyl side chain, providing a heteroaromatic nitrogen for coordination and derivatization. Its hydroxyl and carboxylic acid functionality make it a practical building block for constructing heteroaryl-containing scaffolds, while the racemic (RS) stereochemical composition supports use where stereopurity is not required or where chiral resolution is performed downstream. In chemical and medicinal chemistry workflows, this structure is frequently leveraged to introduce a pyridyl motif alongside an amino-acid-like backbone for SAR studies and intermediate synthesis.
1. Heteroaryl Building Block Synthesis
(RS)-2-Hydroxy-3-(3-pyridyl)-propionic acid is used as an amino-acid-like building block in heteroaryl-containing small-molecule synthesis, particularly when a 3-pyridyl group must be installed with adjacent hydroxyl functionality. Medicinal chemistry groups employ it to generate intermediate fragments for peptidomimetic and constrained analogs, where the hydroxy and carboxyl groups enable further functional-group interconversions prior to final scaffold assembly. Because the product is supplied as a racemate, it is commonly selected for early-stage library synthesis, where throughput and structural diversity are prioritized over stereochemical refinement until later development steps.
2. Chiral Resolution And Stereochemical Studies
(RS)-2-Hydroxy-3-(3-pyridyl)-propionic acid serves as a starting material for chiral resolution workflows and stereochemical method development, since the (RS) composition allows separation into individual enantiomers when stereochemistry becomes critical. Chemical development teams use it to prepare enantiopure derivatives for structure-activity relationship (SAR) investigations, stereochemical profiling, and downstream synthesis of optically defined intermediates. The presence of a pyridine nitrogen and a hydroxyl group also supports formation of diastereomeric derivatives with chiral reagents or auxiliaries, enabling practical routes for analytical or preparative separation.
3. Coordination Chemistry Intermediate
(RS)-2-Hydroxy-3-(3-pyridyl)-propionic acid is frequently incorporated into coordination chemistry and materials-oriented intermediate development due to the combination of a pyridyl nitrogen and an oxygen-bearing side chain. Research groups use it to prepare ligand precursors for metal-binding studies, including ligand frameworks where the pyridine provides directional coordination and the hydroxy functionality supports additional hydrogen-bonding or further derivatization. This makes the compound useful in the development of metal-ligand assemblies, catalyst precursor libraries, and functional materials where amino-acid-like backbones are used to tune solubility, chelation geometry, and post-functionalization options.
4. Pharmaceutical Intermediate Development
(RS)-2-Hydroxy-3-(3-pyridyl)-propionic acid is applied as a practical intermediate for constructing heteroaryl-containing fragments used in pharmaceutical intermediate programs and process chemistry development. Developers use the compound to introduce a 3-pyridyl motif in a controlled manner while retaining functional handles (carboxylic acid and hydroxyl) for conversion into activated derivatives, protected intermediates, or coupling-ready forms later in the synthetic sequence. Its racemic nature supports cost-effective access to the core scaffold during early process and route scouting, with stereochemical control typically addressed in subsequent steps if required by the target structure.
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