H-(2S,4R)-gamma-Hydroxy-Glu-OH

H-(2S,4R)-gamma-Hydroxy-Glu-OH is a stereochemically defined glutamic acid derivative bearing a side-chain gamma-hydroxyl group, with the (2S,4R) configuration corresponding to the alpha-amino stereocenter and the stereogenic center associated with the extended side chain. The molecule contains a free carboxylic acid at the C-terminus and a primary amino group at the alpha position, enabling direct participation in peptide coupling chemistry and subsequent derivatization. The gamma-hydroxyl functionality introduces an additional hydrogen-bonding handle and a reactive alcohol site that can be protected, activated, or converted into ether, ester, or leaving-group derivatives. As an amino acid-based intermediate, the compound's polar zwitterionic character and stereodefined geometry support incorporation into peptide analogs and stereoselective synthesis of functionalized glutamate motifs.

1. Peptide Synthesis

H-(2S,4R)-gamma-Hydroxy-Glu-OH is used in peptide building-block preparation where the alpha-amino and C-terminal carboxyl groups support amide bond formation under standard peptide coupling conditions. The gamma-hydroxyl side chain can be protected as an ether or ester during chain assembly to prevent side reactions during N-protection and coupling steps, then selectively deprotected to reveal the functional alcohol for downstream chemistry. The (2S,4R) stereochemical definition helps maintain the intended glutamate-derived stereochemical pattern in peptide sequences and peptidomimetic scaffolds. The resulting gamma-hydroxyglutamate-containing peptides and peptide fragments can be used to probe structure-function relationships and generate reactive handles for further conjugation.

2. Amino Acid Modification

H-(2S,4R)-gamma-Hydroxy-Glu-OH serves as a substrate for side-chain functionalization strategies that exploit the alcohol at the gamma position. The hydroxyl group can be converted into activated esters, carbonate/urethane derivatives, or ether-linked motifs, while the carboxylic acid and amino functionality can be temporarily protected to enable chemoselective transformations. Stereochemical control at the (2S,4R) centers supports the synthesis of defined analogs for enzymatic recognition studies and for mapping how gamma-hydroxyl substitution influences binding or reactivity. The compound therefore functions as a biochemical research intermediate for producing functionalized glutamate derivatives used in synthetic organic chemistry and applied molecular design.

3. Chemical Biology Conjugation

H-(2S,4R)-gamma-Hydroxy-Glu-OH is suitable for chemical biology workflows that require a polar, stereodefined amino acid handle for bioconjugation chemistry. The gamma-hydroxyl group can be transformed into linkers bearing activated leaving groups or orthogonal protecting groups, allowing attachment to targeting moieties, affinity tags, or reporter groups while preserving the glutamate backbone's recognition features. The presence of both amino and carboxyl groups enables formation of stable amide or ester linkages after appropriate protection and activation, supporting modular conjugate construction. Downstream derivatives can be applied to biomolecule labeling, probe synthesis, and generation of conjugation-ready intermediates for studying amino acid-mediated interactions.

4. Enzyme Studies

H-(2S,4R)-gamma-Hydroxy-Glu-OH is used in enzyme substrate and inhibitor design contexts where glutamate-like geometry and a gamma-hydroxyl substituent can modulate enzyme active-site interactions. The stereochemically defined amino acid framework provides a consistent spatial arrangement for hydrogen-bonding and electrostatic contacts, while the gamma-hydroxyl can participate as a donor/acceptor or be derivatized to tune interaction strength. Protection-group strategies that mask the amino or carboxyl functionality can be employed to generate analogs that probe specificity, including derivatives that mimic transitional states or alter phosphorylation/oxidation susceptibility. The compound thus supports biochemical research intermediate preparation for mechanistic studies of enzymes that recognize glutamate-derived motifs.

5. Pharmaceutical Manufacturing

H-(2S,4R)-gamma-Hydroxy-Glu-OH is relevant to pharmaceutical intermediate preparation and process chemistry routes that require stereodefined amino acid derivatives for peptide-based or peptidomimetic manufacturing. The free carboxylic acid and amino group enable conversion into protected forms compatible with industrial peptide coupling sequences, while the gamma-hydroxyl provides a functional handle for controlled downstream derivatization such as linker installation or solubility tuning. The stereochemical integrity at (2S,4R) supports reproducible synthesis of defined intermediates used in scale-up planning and analytical method development. The compound can be employed to generate well-defined glutamate analogs for specialty chemical production where functional-group management and stereochemical fidelity are central to manufacturing consistency.

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