D-erythro-4-hydroxyglutamic acid is a D-configured, erythro-stereochemically specified amino acid derivative belonging to the glutamic acid family, featuring a four-carbon side chain terminating in a secondary 4-hydroxy substituent. The molecule bears a free amino group and a carboxylic acid group on the α-carbon and side-chain, with the additional hydroxyl functionality providing hydrogen-bonding and polarity that can influence peptide incorporation and chemical derivatization. In research and peptide chemistry workflows, it is used as a defined building block for preparing hydroxy-functionalized amino acid residues in peptide synthesis, as well as for structure-activity studies and analytical method development where a stereochemically characterized hydroxyglutamate motif is required.
CAT No: CP06903
D-erythro-4-hydroxyglutamic acid is a D-configured, four-carbon amino acid bearing a stereogenic center at the C4 position and a secondary alcohol at the 4-hydroxy side chain, together with a free carboxylic acid and a primary amino group. The D-erythro relationship between the amino-bearing backbone and the hydroxy substituent defines a defined three-dimensional hydrogen-bonding pattern that can influence recognition in enzymatic and receptor-like binding contexts. The molecule's functional groups support controlled derivatization through amino protection for peptide coupling, carboxyl activation for ester or amide formation, and alcohol chemistry for further side-chain elaboration. As a chiral amino acid with a reactive hydroxyl handle, D-erythro-4-hydroxyglutamic acid serves as a stereochemically defined intermediate for building hydroxyl-functionalized amino acid motifs and for preparing downstream analogs used in peptide and biochemical research.
1. Peptide Synthesis
D-erythro-4-hydroxyglutamic acid is applied in peptide building-block preparation where the amino group can be protected (commonly as an N-protected derivative) and the carboxyl group can be converted into an activated coupling partner for amide bond formation. The side-chain hydroxyl at C4 enables orthogonal protection strategies, allowing selective deprotection to generate a free alcohol for later functionalization while the backbone remains protected during chain assembly. The D-erythro stereochemistry can be preserved through protection and coupling steps, supporting synthesis of hydroxylated glutamate-containing sequences and peptide analogs. Hydroxyl-bearing glutamate residues prepared from this intermediate can then be incorporated into peptide scaffolds for structure-function studies and synthetic methodology development in amino acid coupling chemistry.
2. Chemical Biology
D-erythro-4-hydroxyglutamic acid is suitable for chemical biology workflows that require a chiral, hydroxyl-functionalized amino acid to probe recognition elements in enzyme studies or binding assays. The combination of a carboxylate, an amino functionality (after appropriate protection/deprotection), and a stereodefined secondary alcohol supports targeted derivatization into conjugatable handles such as activated esters, carbonate/urethane-type linkers, or protected alcohol intermediates for subsequent labeling. The defined D-configuration and erythro stereorelationship can be leveraged to evaluate stereochemical effects on substrate-like behavior or on molecular recognition in assay systems. Downstream derivatives prepared from this amino acid can serve as biochemical research intermediates for generating labeled probes, immobilizable substrates, or hydroxylated analog libraries for mechanistic investigation.
3. Side-Chain Functionalization
D-erythro-4-hydroxyglutamic acid is used in side-chain functionalization chemistry because the C4 hydroxyl group can undergo controlled transformations while the amino acid backbone is managed through protection-group strategies. Alcohol reactivity supports conversion into ethers, esters, or leaving-group-bearing intermediates, enabling installation of additional polarity, steric features, or orthogonal functional groups that can be carried into peptide or small-molecule frameworks. The carboxylic acid and amino group can be selectively protected to direct functionalization toward the hydroxyl without compromising stereochemistry at the chiral center. Resulting hydroxyl-modified glutamate derivatives can be employed as process-ready intermediates for fine chemical synthesis, peptidomimetic construction, and stereochemically defined structure elaboration.
4. Peptidomimetics And SAR
D-erythro-4-hydroxyglutamic acid supports peptidomimetic and SAR-oriented synthesis where hydroxylated glutamate motifs are incorporated to tune hydrogen-bonding capacity and conformational preferences. The stereogenic D-erythro arrangement provides a defined spatial relationship between the side-chain hydroxyl and the amino acid backbone, which can influence conformational bias and binding interactions in analog series. The amino acid's functional groups can be converted into N- and C-terminally protected forms to enable systematic substitution patterns, including side-chain derivatization followed by controlled deprotection to reveal reactive groups for final scaffold assembly. Hydroxylated analogs derived from this intermediate can be used to generate structure-activity relationship panels and to support fragment-to-lead style optimization in medicinal chemistry research settings.
5. Pharmaceutical Intermediate Preparation
D-erythro-4-hydroxyglutamic acid is relevant to pharmaceutical intermediate preparation because it provides a stereochemically defined chiral amino acid motif with an alcohol handle that can be carried through protected-amino-acid synthesis routes. The presence of both an amino group and a carboxylic acid enables manufacturing-compatible transformations into N-protected amino acid derivatives and activated ester or amide intermediates, while the side-chain hydroxyl can be protected orthogonally to maintain chemoselectivity during sequential steps. D-erythro stereochemistry can be retained through protection and coupling operations, supporting consistent impurity profiles and reproducible downstream synthesis of hydroxyl-functionalized analogs. Prepared derivatives can then serve as intermediates for generating hydroxylated peptide fragments, peptidomimetic building blocks, and other fine chemical structures used in applied chemical manufacturing pipelines.
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