(2S,3R)-2-amino-3-hydroxy-succinic acid is a stereochemically defined amino acid derivative featuring a four-carbon succinic acid backbone bearing an amino group at C2 and a hydroxyl-bearing side chain at C3. The molecule contains both an amino functional group and a carboxyl group, with the (2S,3R) configuration specifying the relative stereochemistry around the amino-bearing and hydroxyl-bearing centers. Its dual functional handles support its use as a building block in peptide and amino acid derivative synthesis and in chemical biology workflows where hydroxy-substituted, stereodefined amino acid motifs are used for structure-activity studies, conjugation, or analytical method development.
CAT No: CP06702
CAS No:6532-76-9
Synonyms/Alias:erythro-beta-Hydroxyasparticacid;(3R)-3-hydroxy-L-asparticacid;erythro-3-Hydroxy-L-asparticacid;UNII-GDV0MSK2SG;Erythro-beta-hydroxy-L-asparticacid;erythro-3-Hydroxy-L-aspartate;(2S,3R)-2-amino-3-hydroxybutanedioicacid;erythro-3-Hydroxy-Ls-asparticacid;Asparticacid,L-threo-beta-hydroxy-;(2S,3R)-2-amino-3-hydroxysuccinicacid;beta-Hydroxyasparticacid;(2S,3R)-2-amino-3-hydroxy-succinicacid;ASPARTICACID,3-HYDROXY-,(erythro)-;6532-76-9;1186-90-9;7298-98-8;GDV0MSK2SG;AC1L23VS;(3R)-3-Hydroxyasparticacid;SCHEMBL336362;erythro-3-hydroxy-Ls-aspartate;CHEBI:17576;CTK4B0789;Erythro-b-hydroxy-l-asparticacid;ZINC901877
(2S,3R)-2-amino-3-hydroxy-succinic acid is a stereodefined, hydroxylated amino acid building block featuring both a primary amino group and a secondary alcohol on a succinic acid framework. Its defined (2S,3R) configuration and di-functional handle make it a useful intermediate for constructing stereochemically controlled amino acid derivatives and for preparing functionalized succinate-based motifs used in chemical biology and medicinal chemistry workflows.
1. Stereocontrolled Amino Acid Derivatives
(2S,3R)-2-amino-3-hydroxy-succinic acid is used as a chiral precursor to generate stereochemically defined amino acid derivatives where the hydroxyl-bearing succinate motif is retained or further functionalized. Researchers in medicinal chemistry and process development commonly incorporate this scaffold into side-chain analogs, constrained building blocks, and derivative libraries aimed at structure-property studies, where the presence of both an amino functionality and a secondary alcohol enables downstream derivatization while maintaining the (2S,3R) stereochemical information.
2. Peptidomimetic And Linker Synthesis
(2S,3R)-2-amino-3-hydroxy-succinic acid serves as a practical building block for peptidomimetic and linker construction that require an amino-bearing, hydroxylated succinate unit to modulate geometry and hydrogen-bonding patterns. Chemical biology groups and custom synthesis teams use it to prepare non-proteinogenic fragments for assembling bioactive peptide analogs, modular conjugation handles, and stereodefined spacer elements in synthetic sequences, leveraging the dual functional groups for attachment to amide-forming partners and for subsequent protection/activation steps during assembly.
3. Chiral Intermediate For Medicinal Chemistry
(2S,3R)-2-amino-3-hydroxy-succinic acid is frequently selected as a chiral intermediate in pharmaceutical intermediate development when a hydroxylated amino succinate motif is required as a downstream precursor to more elaborated heterocycles, amide derivatives, or substituted succinate analogs. Process chemists and medicinal chemistry teams value the defined stereochemistry and the presence of both functional groups for controlled conversion into reactive intermediates used in route scouting, SAR synthesis, and scale-up-oriented intermediate manufacturing where stereochemical fidelity is important.
4. Functionalized Succinate Materials Development
(2S,3R)-2-amino-3-hydroxy-succinic acid is also used in biomaterials and specialty polymer research to introduce a hydroxylated amino succinate functionality into functional monomers or crosslinkable intermediates. Materials scientists employ it to build stereodefined, reactive precursor units that can be further transformed into tethered linkers, surface-reactive components, or scaffold fragments for material functionalization, where the combination of amino and alcohol groups supports chemical coupling strategies during materials formulation and post-synthetic modification.
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