L-erythro-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 at the 3-position (3-hydroxyglutamate). The molecule contains both an amino group and a carboxyl group, and the side-chain hydroxyl introduces polarity and hydrogen-bonding capability, while the "erythro" descriptor indicates the relative stereochemical relationship between the hydroxyl-bearing center and the adjacent stereocenter under the specified configuration. As a free amino acid, it is used as a defined building block for peptide and amino-acid-containing conjugate synthesis and for structure-function studies where a hydroxylated glutamate side chain is required for conformational or hydrogen-bonding effects.
CAT No: CP06802
L-erythro-3-hydroxyglutamic acid is an L-configured, side-chain functionalized amino acid featuring a stereogenic center at C-3 within a glutamate framework and a hydroxyl group positioned for stereochemically defined derivatization. The molecule contains a primary amino functionality and a carboxylic acid, enabling formation of peptide bonds through standard amino acid coupling chemistry after appropriate protection and activation. The additional hydroxyl group can participate in hydrogen bonding and can be selectively protected to control chemoselectivity during peptide assembly or downstream transformations. As a chiral amino acid building block and biochemical research intermediate, it can be converted into protected derivatives, activated esters, or protected amino acid analogs that preserve the erythro stereochemical relationship during synthesis.
1. Peptide Synthesis
L-erythro-3-hydroxyglutamic acid supports peptide building block preparation where the amino and carboxyl groups enable amide bond formation after N-protection and C-terminal activation. The erythro-configured C-3 hydroxyl group can be protected (for example, as an ether) to prevent side reactions during coupling and to allow controlled deprotection after chain assembly. The glutamate backbone length and stereogenic side-chain hydroxyl position can be leveraged to generate peptide segments that mimic phosphorylated or hydroxylated motifs relevant to biomolecular recognition. Downstream use includes construction of hydroxyglutamate-containing peptides for method development, peptide library synthesis, and stereodefined analog generation in peptide chemistry workflows.
2. Chemical Biology
L-erythro-3-hydroxyglutamic acid functions as a chiral chemical biology intermediate for probing hydroxyl-dependent molecular recognition and post-translational modification mimicry. The side-chain hydroxyl group provides a handle for installing labels, affinity tags, or clickable substituents while maintaining the L-erythro stereochemistry that governs three-dimensional presentation. The amino acid's protected forms can be incorporated into peptides or other biomolecule scaffolds to study binding preferences, conformational effects, and functional group contributions to molecular interactions. The resulting hydroxyglutamate-containing probes can be used in biochemical research settings that require stereodefined analogs rather than racemic mixtures.
3. Side-Chain Functionalization
L-erythro-3-hydroxyglutamic acid is suitable for side-chain functionalization strategies that transform the hydroxyl group into chemically differentiated motifs for synthetic diversification. The presence of both an amino acid core and an additional hydroxyl enables orthogonal protection planning, where N-protection and hydroxyl protection can be selected to survive peptide coupling conditions and later be removed selectively. Hydroxyl derivatization can produce esters, ethers, or activated intermediates that participate in further coupling, enabling construction of complex peptidomimetic fragments and stereochemically constrained scaffolds. The stereogenic erythro center helps maintain defined spatial relationships during downstream synthesis of functionalized amino acid derivatives for fine chemical and research intermediate applications.
4. Peptidomimetics And SAR Studies
L-erythro-3-hydroxyglutamic acid can be employed in peptidomimetic construction where the glutamate-like backbone and hydroxyl-bearing side chain enable incorporation into structure-activity relationship studies. The hydroxyl group can be used to tune hydrogen-bonding capacity and polarity, while stereochemical control at the C-3 center supports consistent conformational behavior across analog series. Protected amino acid derivatives derived from L-erythro-3-hydroxyglutamic acid can be assembled into constrained analogs that preserve the relative orientation of the hydroxyl and backbone functionalities. Downstream utility includes generation of stereodefined SAR libraries and analog intermediates for medicinal chemistry campaigns focused on hydroxyl-containing motif optimization.
5. Pharmaceutical Intermediate Preparation
L-erythro-3-hydroxyglutamic acid serves as a chiral amino acid intermediate for manufacturing-oriented synthesis of protected building blocks and downstream functional fragments used in pharmaceutical and specialty chemical supply chains. The amino acid's carboxylic acid and amino group allow conversion into activated derivatives compatible with controlled coupling chemistry, while hydroxyl protection strategies support robust processing through multi-step sequences. The erythro stereochemistry provides a defined chiral element that can be carried through to final intermediates used for constructing larger drug-like molecules or peptide-based candidates. The compound's functional group pattern supports scalable intermediate preparation routes in fine chemical synthesis where stereochemical integrity and orthogonal protection are central to process design.
6. Analytical Research Standards
L-erythro-3-hydroxyglutamic acid can be applied as a reference material precursor for analytical research involving amino acid profiling, stereochemical identification, and method validation. The molecule's distinct hydroxyl-containing glutamate structure enables targeted derivatization approaches for chromatographic or spectrometric detection, including conversion to protected or derivatized forms that improve analytical response. N-protected and hydroxyl-protected derivatives can also serve as standards for monitoring peptide hydrolysis, side-chain stability, or derivatization efficiency in analytical workflows. Downstream relevance includes preparation of calibration standards and structural verification intermediates that support reliable characterization of hydroxyglutamate-containing compounds in research and industrial quality control contexts.
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