D-erythro-3-hydroxyglutamic acid is a D-configured, non-proteinogenic hydroxy-substituted glutamic acid derivative bearing an erythro relationship between the 3-hydroxyl-bearing carbon and the adjacent stereocenter within the five-carbon side chain. The molecule contains both an amino group and a carboxyl group characteristic of amino acids, with a secondary hydroxyl side-chain functionality that can participate in hydrogen bonding and can serve as a handle for further chemical derivatization. In biochemical and synthetic research, it is used as a defined building block for preparing hydroxy-functional amino acid and peptide analogues and as a substrate or reference compound in studies that examine structure-property relationships involving hydroxylated glutamate motifs.
CAT No: CP06803
D-erythro-3-hydroxyglutamic acid is a D-configured, hydroxy-substituted glutamic acid derivative featuring a chiral 3-hydroxyl-bearing side chain and a second stereocenter within the glutamate skeleton. The molecule contains a free α-amino functionality and two carboxylic acid groups (or corresponding protected forms during synthesis), enabling salt formation and controlled reactivity in peptide-coupling and derivatization workflows. The erythro relationship between the 3-hydroxyl and the backbone substituents provides stereochemical definition that can influence hydrogen-bonding patterns and conformational preferences in downstream analogs. The hydroxyl and carboxyl groups can be selectively protected (e.g., esterification or hydroxyl protection) to support orthogonal peptide assembly, while the amino group can be protected as an N-acyl/urethane-type handle for peptide building block preparation and subsequent deprotection.
1. Peptide Synthesis
D-erythro-3-hydroxyglutamic acid supports peptide construction and amino acid incorporation strategies in research-grade peptide synthesis by providing a glutamate backbone with a stereodefined 3-hydroxyl side chain. The presence of two carboxyl groups and an amino group enables controlled use of N-protection for coupling compatibility and C- or side-chain functional group protection to avoid side reactions during amide bond formation. Orthogonal protection of the 3-hydroxyl (and selective masking of one carboxyl group) can be applied to install the residue at defined positions within protected amino acid sequences. The resulting hydroxyglutamate-containing peptides serve as substrates for studying hydroxy-side-chain recognition, as scaffolds for peptidomimetic design, and as intermediates for generating further functionalized analogs through hydroxyl-directed transformations.
2. Chemical Biology Probes
D-erythro-3-hydroxyglutamic acid is suitable for chemical biology workflows that require stereodefined, polar amino acid motifs for molecular recognition studies. The 3-hydroxyl group provides a hydrogen-bond donor/acceptor site that can be exploited for conjugation chemistry after selective activation or protection-state control, while the glutamate carboxylate(s) support ionic interactions and mimicry of acidic residues in binding interfaces. N- and O-protection strategies can be used to generate peptide conjugates, linker-bearing derivatives, or labeled analogs where the stereochemistry is retained from the D-erythro starting material. Downstream utilities include preparation of receptor-binding probes, enzyme interaction mimics, and structure-activity relationship (SAR) test compounds where hydroxyglutamate stereochemistry is a defined variable.
3. Peptidomimetics And SAR Studies
D-erythro-3-hydroxyglutamic acid functions as a chiral precursor for peptidomimetic construction and SAR-focused medicinal chemistry research intermediate preparation. The glutamate framework with a stereodefined 3-hydroxyl substituent can be converted into constrained or derivatized analogs that preserve key polar features while enabling systematic modification of side-chain functionality. Protection-group planning for the hydroxyl and carboxyl groups supports stepwise assembly of analog libraries, including conversion to activated esters, amide derivatives, or protected intermediates compatible with fragment coupling. The stereochemical fidelity of the erythro configuration can be maintained through protected amino acid stages, enabling comparative studies of stereoisomer effects and side-chain hydrogen-bonding contributions in SAR campaigns.
4. Enzyme Substrate And Inhibitor Design
D-erythro-3-hydroxyglutamic acid can be employed in enzyme studies where hydroxy-substituted acidic residues serve as substrate analogs or binding-state mimics. The amino acid's dual carboxyl functionality and stereodefined hydroxyl group can participate in enzyme active-site recognition through electrostatic interactions and directional hydrogen bonding. Selective protection of one carboxyl group and controlled N-protection can enable synthesis of peptide-like inhibitors, tethered analogs, or hydroxyglutamate-containing fragments that remain compatible with biochemical assay formats. The compound's chiral architecture supports mechanistic probing of stereochemical requirements and side-chain participation, and it can feed downstream derivatization to generate multiple analogs for inhibitor profiling and substrate specificity studies.
5. Process Chemistry Intermediate
D-erythro-3-hydroxyglutamic acid is applicable as a chiral amino acid intermediate in process chemistry and fine chemical synthesis where orthogonal protection and predictable functional group interconversions are required. The amino and carboxylic acid groups allow formation of isolable protected derivatives (e.g., N-protected forms and selective ester/ether masking of the hydroxyl) that can be handled as defined intermediates in multi-step manufacturing routes. The stable stereochemical identity of the D-erythro configuration supports downstream conversion into protected amino acid building blocks for peptide coupling or into activated derivatives for further functionalization. Industrially relevant downstream uses include preparation of hydroxyglutamate-containing specialty intermediates for large-scale peptide analog synthesis, as well as supply of stereodefined building blocks for consistent batch-to-batch performance in synthetic programs.
If you have any peptide synthesis requirement in mind, please do not hesitate to contact us at . We will endeavor to provide highly satisfying products and services.
Creative Peptides is a trusted CDMO partner specializing in high-quality peptide synthesis, conjugation, and manufacturing under strict cGMP compliance. With advanced technology platforms and a team of experienced scientists, we deliver tailored peptide solutions to support drug discovery, clinical development, and cosmetic innovation worldwide.
From custom peptide synthesis to complex peptide-drug conjugates, we provide flexible, end-to-end services designed to accelerate timelines and ensure regulatory excellence. Our commitment to quality, reliability, and innovation has made us a preferred partner across the pharmaceutical, biotechnology, and personal care industries.
Read More