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

H-(2S,4S)-gamma-Hydroxy-Glu-OH is a stereodefined glutamic acid derivative bearing a side-chain gamma-hydroxyl group, with the free carboxylic acid functionality preserved for downstream coupling and salt formation. The molecule contains an α-amino acid backbone (H on the N-terminus) and two carboxyl-related reactive sites typical of glutamate chemistry, while the additional secondary alcohol at the gamma position introduces hydrogen-bonding capacity and selective derivatization handles. The (2S,4S) stereochemistry fixes the relative configuration around the α-carbon and the gamma-substituted center, enabling stereocontrolled incorporation into peptide sequences or conversion into chiral intermediates. The hydroxyl and amino acid functional groups can participate in protected-amino-acid strategies, esterification/amide formation, and selective oxidation or substitution routes that are compatible with amino acid and peptide synthetic workflows.

1. Peptide Synthesis

H-(2S,4S)-gamma-Hydroxy-Glu-OH serves as a glutamate-based peptide building block for constructing peptide chains that require a gamma-hydroxyl side chain for hydrogen-bonding and stereochemical recognition. The free carboxylic acid and amino functionality support standard peptide coupling logic after appropriate protection of the N-terminus and carboxyl group when needed, while the gamma-alcohol can be protected (for example, as an ether) to prevent side reactions during amide bond formation. The defined (2S,4S) stereocenters enable incorporation of a specific stereochemical motif into peptides and peptide analogs, supporting structure-activity relationship studies that depend on side-chain orientation. Downstream, the gamma-hydroxyl can be retained for biochemical interaction studies or converted into functional derivatives for further peptide diversification.

2. Amino Acid Derivatization

H-(2S,4S)-gamma-Hydroxy-Glu-OH is suitable for amino acid derivatization chemistry where the gamma-hydroxyl provides a handle for selective functional group transformation. The amino acid framework allows conversion into esters, amides, or activated derivatives for controlled reactivity in synthetic sequences, while the side-chain alcohol can be oxidized to a ketone, transformed into leaving-group derivatives, or substituted to install alternative substituents at the gamma position. The stereochemical integrity of the (2S,4S) centers supports the preparation of chiral intermediates for downstream medicinal chemistry, peptidomimetic scaffolds, and stereodefined structure libraries. The resulting derivatives can function as intermediates for fine chemical synthesis and as building blocks for subsequent coupling or cyclization steps.

3. Chemical Biology Probes

H-(2S,4S)-gamma-Hydroxy-Glu-OH can be applied in chemical biology workflows that require amino acid side-chain functionality for biomolecular recognition and labeling chemistry. The gamma-hydroxyl enables conjugation strategies based on selective protection/deprotection and subsequent functionalization, while the glutamate-like backbone supports incorporation into peptide tags, affinity handles, or substrate analogs for enzyme-focused studies. The stereodefined amino acid can be used to generate stereochemically consistent probe analogs that help evaluate how side-chain geometry and hydrogen-bonding patterns influence binding or processing. Downstream, derivatized forms can be routed into bioconjugation-ready intermediates compatible with peptide-based probe construction and analytical method development.

4. Enzyme Substrate Studies

H-(2S,4S)-gamma-Hydroxy-Glu-OH is applicable to enzyme substrate or inhibitor design efforts where glutamate-like recognition motifs and a gamma-hydroxyl side chain can modulate enzyme active-site interactions. The presence of both amino acid carboxyl functionality and the stereochemically fixed gamma-alcohol supports the preparation of substrate analogs that mimic key interaction elements while maintaining defined stereochemistry. Protected amino acid derivatives derived from this compound can be incorporated into peptide substrates, allowing evaluation of processing steps that depend on side-chain hydroxyl orientation and hydrogen-bonding. The resulting stereodefined intermediates can also be used to generate mechanistic probes and to support SAR studies in enzyme substrate specificity mapping.

5. Pharmaceutical Manufacturing Intermediates

H-(2S,4S)-gamma-Hydroxy-Glu-OH can function as a chiral amino acid intermediate in pharmaceutical manufacturing routes that require stereodefined hydroxylated glutamate motifs. The amino acid backbone supports conversion into protected forms suitable for peptide coupling chemistry, while the gamma-hydroxyl can be selectively protected to control chemoselectivity during multistep synthesis. The defined (2S,4S) stereochemistry helps maintain product stereochemical requirements through downstream activations, salt formation, and coupling operations that are typical of fine chemical and pharmaceutical intermediate preparation. The compound's functional group set enables manufacturing-friendly transformations into activated intermediates for peptide-based intermediates, peptidomimetic fragments, and stereochemically consistent synthetic building blocks.

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