2-amino-3-hydroxy-succinic acid is a hydroxy-substituted dicarboxylic amino acid featuring both an amino group and two carboxylic acid functionalities within a succinic acid framework, with a hydroxyl substituent at the 3-position. The molecule bears a primary amino group alongside carboxyl groups that can exist in different protonation states and a secondary alcohol that can participate in hydrogen bonding and serve as a handle for further derivatization. In biochemical and synthetic research contexts, it functions as a chemically defined amino acid building block or precursor for preparing more complex amino acid derivatives, including protected forms and conjugatable analogues used in peptide-related intermediate synthesis, structure-reactivity studies, and analytical method development.
CAT No: CP06701
2-amino-3-hydroxy-succinic acid is a polar, di-functional amino acid building block featuring both a primary amino group and a secondary hydroxyl on the carbon backbone, along with a second carboxyl functionality typical of hydroxy-substituted dicarboxylic amino acid derivatives. Its high hydrogen-bonding capacity and multiple ionizable groups make it useful in chemical biology workflows where controlled incorporation of hydroxyl and amino functionality is required. In synthetic and analytical settings, it is handled as a reactive precursor for preparing defined amino alcohol and amino acid-like motifs used in downstream coupling, derivatization, and reference-material production.
1. Peptidomimetic Building Block
2-amino-3-hydroxy-succinic acid is used as a specialty amino acid building block for constructing peptidomimetic and constrained peptide-like structures that incorporate both amino and hydroxyl functionality within a dicarboxylic framework. Medicinal chemistry and chemical biology teams often select this motif to introduce a defined hydrogen-bonding pattern and additional polar handles into short peptide analogs, which can be valuable for structure-activity relationship studies and for generating libraries of backbone-modified ligands. Because it contains two carboxyl groups and a hydroxyl-bearing carbon, it supports downstream functional-group management during fragment assembly and coupling to other protected amino acid units.
2. Chemical Derivatization Reagent
2-amino-3-hydroxy-succinic acid serves as a practical derivatization precursor for analytical chemistry and materials-related synthesis where a defined amino plus hydroxy functionality is needed to tune reactivity and improve detectability. Researchers use it to prepare standardized derivatives for method development, including derivatization strategies that benefit from introducing an amino group for subsequent tagging or from leveraging the hydroxyl group for controlled functional transformation. In industrial R&D contexts, it is also employed to access amino alcohol-containing intermediates and to build multifunctional scaffolds that can be carried forward into polymerizable or crosslinkable systems after appropriate activation of the carboxyl groups.
3. Pharmaceutical Intermediate Development
2-amino-3-hydroxy-succinic acid is commonly incorporated into pharmaceutical intermediate development programs as a multifunctional precursor for heteroatom-rich intermediates, especially when a hydroxyl-bearing amino motif is required for later coupling steps. Process and synthetic chemistry groups use it to introduce polar functionality early in a route, enabling subsequent conversion into activated carboxylic derivatives, protected intermediates, or other amino acid-like fragments that can be assembled into larger, more complex molecules. Its dicarboxylic character provides two handles for selective downstream transformation planning, supporting the creation of well-defined intermediates used in custom synthesis and scale-up-oriented workflows.
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