(2R,3R)-2-amino-3-hydroxy-succinic acid is a free amino acid derivative featuring a four-carbon succinic acid backbone bearing an amino group at C2 and a hydroxyl-bearing stereogenic center at C3, with stereochemistry specified as (2R,3R). The molecule contains both an amino functional group and a carboxylic acid functional group (as part of the dicarboxylic acid framework), and the side-chain-like hydroxyl substituent provides a polar hydrogen-bonding handle that can participate in aqueous solubility and coordination chemistry. In research and synthesis contexts, it is used as a defined building block for preparing modified amino acid and peptide-related structures, including incorporation into peptide analogues or as a precursor for further functionalization of the hydroxy and carboxyl groups.
CAT No: CP06705
CAS No:16417-36-0
Synonyms/Alias:(2R,3R)-2-amino-3-hydroxysuccinicacid;(R,R)-3-hydroxyasparticacid;D-threo-3-hydroxyasparticacid;threo-D-3-hydroxyasparticacid;CHEBI:60897;threo-3-hydroxy-D-asparticacid;D-threo-beta-hydroxyasparticacid;(3R)-3-hydroxy-D-asparticacid;threo-beta-hydroxy-D-asparticacid;16417-36-0;(2R,3r)-2-amino-3-hydroxy-succinicacid;(2R,3R)-2-amino-3-hydroxybutanedioicacid;threo-2-Amino-3-hydroxysuccinicacid;4294-45-5;D,L-threo-beta-HydroxyAsparticAcid;DL-threo--Hydroxyasparticacid;CHEMBL1256517;SCHEMBL12648656;DL-threo-|A-Hydroxyasparticacid;ZINC3875092;Asparticacid,3-hydroxy-,threo-;MFCD00036749;AKOS017344538;D-Asparticacid,3-hydroxy-,(3R)-;AJ-46411
(2R,3R)-2-amino-3-hydroxy-succinic acid is a stereochemically defined amino acid derivative featuring a primary amino group and a secondary alcohol on a succinic acid backbone. Its (2R,3R) configuration and dual functional handles make it a useful building block for constructing polar, hydroxyl-containing motifs in peptide-like scaffolds and small-molecule intermediates. In research and industrial settings, it is typically selected when a controlled chiral aminoalcohol functionality is required for downstream derivatization, coupling, or stereodefined synthesis.
1. Chiral Building Block Synthesis
(2R,3R)-2-amino-3-hydroxy-succinic acid is used as a chiral aminoalcohol building block for preparing stereodefined intermediates in medicinal chemistry and process development. Synthetic teams incorporate its (2R,3R) stereochemistry to introduce a hydroxyl-bearing carbon next to an amino-functional center, supporting the creation of polar side-chain analogs, constrained fragments, and functionalized linkers. The molecule's free amino and hydroxyl groups enable straightforward conversion into protected coupling partners or activated derivatives used in subsequent assembly steps for complex small molecules.
2. Peptidomimetic And Linker Design
(2R,3R)-2-amino-3-hydroxy-succinic acid serves as a structural element in peptidomimetic and peptide-like scaffold design where an amino acid-derived segment with an alcohol functionality is needed. Researchers use it to introduce hydroxyl-containing stereocenters that can influence conformation and provide handles for later functional modification, such as further derivatization or attachment to larger constructs. This makes it a practical choice for custom peptide synthesis workflows and for building linker units in structure-activity relationship studies that require precise stereochemical control of the aminoalcohol motif.
3. Pharmaceutical Intermediate Development
(2R,3R)-2-amino-3-hydroxy-succinic acid is commonly employed as an intermediate for manufacturing routes that require a chiral, multifunctional precursor with both nitrogen and oxygen functionality. Process chemists value it for enabling downstream transformations that depend on orthogonal reactivity between the amino and hydroxyl groups, allowing sequential protection/activation strategies during intermediate elaboration. Its succinic acid framework also supports scalable synthesis of polar intermediates used to access hydroxylated amine-containing chemotypes in pharmaceutical intermediate libraries.
4. Analytical Derivatization Standards
(2R,3R)-2-amino-3-hydroxy-succinic acid can be used in analytical method development and reference material preparation where a defined chiral aminoalcohol is required for derivatization-based workflows. Analytical laboratories select it to create consistent derivatives that improve interpretability in stereochemical or functional-group-specific analyses, particularly when monitoring amino and hydroxyl-containing fragments in complex mixtures. Because the compound's stereochemistry is fixed, it supports reproducible comparison across batches during method qualification and intermediate characterization.
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