3-hydroxyglutamic acid is a naturally occurring amino acid derivative of the glutamic acid family, featuring a five-carbon backbone with a side-chain hydroxyl substituent at the 3-position relative to the α-amino and α-carboxyl groups. The molecule contains both an amino functional group and a carboxylic acid, and its additional secondary alcohol side chain can participate in hydrogen bonding and serve as a site for further chemical derivatization while maintaining the glutamate-like dicarboxylate/acid-base character typical of this amino acid class. In biochemical and synthetic research, it is used as a defined building block or substrate analogue for preparing modified peptides, studying side-chain hydroxyl effects in structure-activity or structure-function experiments, and supporting analytical method development that distinguishes closely related glutamate derivatives.
CAT No: CP06801
CAS No:533-62-0
Synonyms/Alias:2-amino-3-hydroxypentanedioicacid;533-62-0;3-hydroxyglutamicacid;AC1NAKXK;3-OH-Glu-OH;SCHEMBL300199;CTK8J0928;2-azanyl-3-oxidanyl-pentanedioicacid;AM004085;A829540
3-hydroxyglutamic acid is an amino acid derivative featuring a hydroxylated side chain, providing an additional polar functional handle beyond the primary amino and carboxylic acid groups. As a research-grade building block, it is frequently used to introduce hydroxyglutamate motifs into synthetic peptides and to support chemical biology and analytical workflows where the presence of a hydroxyl-bearing glutamate unit is required. Its well-defined functionality also makes it a practical reference material for method development and quantitative measurements in studies that track hydroxyglutamate-containing species.
1. Peptide And Peptidomimetic Synthesis
3-hydroxyglutamic acid is used by peptide chemistry groups to incorporate hydroxyglutamate residues into custom peptides and peptidomimetic scaffolds. The hydroxylated side chain provides a site for hydrogen bonding and polarity modulation, which is valuable when researchers are probing structure-property relationships, conformational preferences, or the behavior of glutamate-like motifs in synthetic sequences. In practice, it supports downstream assembly workflows where glutamate-derived side-chain functionality is needed rather than a standard unmodified glutamate residue.
2. Chemical Biology Probe Development
3-hydroxyglutamic acid is employed in chemical biology research where hydroxyglutamate chemistry is leveraged to generate labeled analogs, affinity reagents, or substrate-like tools for studying hydroxyglutamate-associated processes at the molecular level. The presence of the side-chain hydroxyl group enables derivatization strategies that can introduce tags for detection or immobilization, allowing researchers to build reagents that report on incorporation, recognition, or handling of hydroxyglutamate motifs in biochemical experiments. This makes it a useful starting amino acid building block for constructing hydroxyglutamate-bearing probes used in mechanistic and pathway-focused studies.
3. LC-MS And Quantitative Reference Standards
3-hydroxyglutamic acid is widely used as an analytical reference material for LC-MS workflows that quantify hydroxyglutamate-containing analytes or monitor hydroxyglutamate-related species in complex matrices. Laboratories developing metabolomics or targeted amino-acid panels rely on authentic hydroxyglutamic acid to confirm retention behavior, support calibration, and improve confidence in peak assignment for hydroxylated glutamate forms. Because the compound contains the characteristic hydroxylated side chain, it is particularly relevant for distinguishing hydroxyglutamate species from closely related glutamate or other amino acid standards during method validation and routine quantitation.
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