L-Glutamic acid diallyl ester hydrochloride is a glutamate-derived amino acid ester in which the α-carboxyl group and the side-chain γ-carboxyl group of L-glutamic acid are both esterified with allyl (diallyl) groups, forming a diallyl ester hydrochloride salt. The molecule retains an amino functionality and an esterified carboxyl framework, with the hydrochloride counterion associated to the basic amino group, while the allyl ester motifs provide hydrolytically and chemically addressable handles for further derivatization. In peptide and chemical synthesis contexts, this protected glutamate ester form is used as a precursor that can be manipulated under conditions compatible with ester handling, including subsequent transformations of the allyl ester groups to access glutamate-containing intermediates or to prepare labeled and conjugatable glutamate derivatives.
CAT No: CP00760
CAS No:20845-16-3
Synonyms/Alias:20845-16-3;(S)-diallyl2-aminopentanedioatehydrochloride;H-GLU(OALL)-OALLHCL;L-Glutamicaciddiallylesterhydrochloride;MolPort-028-959-957;7145AH;AKOS024462493;AM81745;AK161881;KB-53196;SC-09528;4CH-023288;FT-0601850;ST24036279;K-6029;1128075-52-4
L-Glutamic acid diallyl ester hydrochloride is an L-configured glutamate derivative in which the side-chain carboxylate and the α-carboxyl group are both masked as diallyl esters, while the material is provided as a hydrochloride salt to support handling and controlled reactivity. The molecule retains the stereogenic α-carbon characteristic of L-glutamate and presents an amino functionality that is typically present as a salt-associated, protected form suitable for downstream transformations. Two allyl ester groups introduce alkene handles that can undergo selective deprotection or functional group conversion under conditions compatible with amino acid ester chemistry, while the diallyl motif supports orthogonal manipulation relative to other protecting-group strategies. The resulting glutamate-based intermediate participates in peptide-related assembly logic and can be routed toward protected amino acid synthesis, side-chain functionalization, and polymerizable or crosslinkable glutamate derivatives.
1. Protected Glutamate Ester Synthesis
L-Glutamic acid diallyl ester hydrochloride is used in protected amino acid chemistry and chiral intermediate preparation where glutamate must be carried through multi-step sequences without premature hydrolysis of carboxyl groups. The diallyl ester masking of both α- and side-chain carboxylates provides ester-stabilized functionality that can be selectively removed or transformed to regenerate carboxylic acid handles for coupling chemistry. The L-stereocenter is maintained through esterification and subsequent manipulations, supporting stereochemically defined glutamate building blocks for peptide coupling chemistry and derivatization workflows. Downstream processing can convert the regenerated acids into activated forms for amide bond formation or into protected amino acid derivatives tailored to specific peptide synthesis strategies.
2. Peptide Coupling Building Block
L-Glutamic acid diallyl ester hydrochloride serves as a glutamate-derived peptide building block precursor in peptide synthesis workflows that require controlled exposure of carboxyl groups during N- and C-terminal construction. The presence of ester-protected carboxyl groups enables compatibility with peptide coupling conditions that may otherwise damage free acids, while the hydrochloride salt form can help manage amine protonation states during protection and activation steps. Diallyl ester functionality can be used to implement orthogonal deprotection logic, allowing sequential unmasking of glutamate carboxylates to support selective side-chain incorporation in peptide analogs. The resulting glutamate acids can be used to generate glutamyl residues in linear peptides, cyclic peptides, and protected peptide fragments used for biochemical research and synthetic organic chemistry.
3. Side-Chain Functionalization
L-Glutamic acid diallyl ester hydrochloride supports side-chain functionalization programs in chemical biology and materials-oriented synthesis where allyl-bearing glutamate scaffolds are converted into diversified carboxyl-reactive or crosslinkable derivatives. The diallyl ester groups provide alkene-containing handles that can be transformed into alternative functional motifs, enabling access to glutamate analogs with modified reactivity profiles for conjugation chemistry and scaffold diversification. The L-glutamate backbone preserves stereochemical identity, which is relevant when downstream steps require stereodefined amino acid residues for molecular recognition studies or enzyme-substrate mimic design. Generated derivatives can feed into peptidomimetic construction, polymer modification, or functional material precursor preparation where glutamate-derived functionality is required to tune solubility, charge density, or chemical reactivity.
4. Polymer And Crosslinkable Monomers
L-Glutamic acid diallyl ester hydrochloride is applied in functional materials and specialty chemical production as a glutamate-based monomer precursor for polymer modification and crosslinkable network formation. The diallyl ester motif introduces polymerizable alkene functionality while retaining glutamate's carboxyl-derived ester framework that can later be converted to acid or activated ester forms for post-polymer functionalization. The hydrochloride salt form can assist in controlling ionic character during formulation and processing steps that involve amino acid derivatives. Downstream conversion routes can yield glutamate-containing polymers, hydrogels, or surface-reactive materials that incorporate amino acid chemistry into industrially relevant macromolecular architectures.
5. Process Chemistry Intermediate
L-Glutamic acid diallyl ester hydrochloride is suitable for process chemistry intermediate preparation where stable ester protection of glutamate carboxyl groups is required to manage reactivity across manufacturing-relevant multi-step sequences. The diallyl ester protection pattern can be leveraged to design stepwise deprotection or conversion strategies that reduce side reactions associated with free carboxylic acids under coupling and derivatization conditions. The defined L-configuration supports consistent downstream stereochemical outcomes for glutamate-derived intermediates used in fine chemical synthesis and peptide manufacturing supply chains. Generated glutamate acids and activated derivatives can then be routed into peptide building blocks, biochemical research reagents, or further industrial intermediate production for specialty chemical applications.
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