L-Glutamic acid di-tert.butyl ester hydrochloride is a glutamate-derived amino acid ester in which the side-chain carboxyl group and the α-carboxyl group are both converted to tert-butyl ester forms, while the molecule retains an amino functionality characteristic of an amino acid framework. The hydrochloride salt form indicates protonation of the amino group as a chloride-associated species, and the tert-butyl ester groups are acid-labile protecting/derivatizing groups that mask carboxylate charge and alter solubility and chemoselectivity during handling. In peptide and amino-acid derivative synthesis, this di-tert-butyl ester hydrochloride is employed as a protected glutamate building block to control carboxyl reactivity and to support stepwise assembly or further functionalization of glutamate side-chain chemistry in solution-phase or solid-phase workflows.
CAT No: CP00766
CAS No:32677-01-3
Synonyms/Alias:32677-01-3;L-Glutamicaciddi-tert-butylesterhydrochloride;(S)-Di-tert-butyl2-aminopentanedioatehydrochloride;H-Glu(OtBu)-OtBu.HCl;H-GLU(OTBU)-OTBUHCL;NSC94681;H-Glu(OtBu)-OtBuinvertedexclamationmarkcurrencyHCl;di-tert-butyll-glutamatehydrochloride(1:1);ditert-butyl(2S)-2-aminopentanedioatehydrochloride;1,5-di-tert-butyl(2S)-2-aminopentanedioatehydrochloride;L-Glutamicacid,bis(1,1-dimethylethyl)ester,hydrochloride;C13H26ClNO4;H-Glu(OtBu)-OtBuCl;PubChem16067;AC1Q5XIZ;H-Glu(OtBu)-OtBu?HCl;AC1L4L1A;H-Glu(OBut)-OBut??HCl;SCHEMBL18476;KSC222I7J;G7501_SIGMA;73134_FLUKA;CTK1C2474;LFEYMWCCUAOUKZ-FVGYRXGTSA-N;MolPort-003-938-785
L-Glutamic acid di-tert.butyl ester hydrochloride is a protected L-glutamate derivative in which both carboxyl groups are masked as tert-butyl esters and the amino functionality is retained as a protonated species associated with hydrochloride. The molecule therefore presents a chiral glutamate backbone with two esterified acidic sites, enabling controlled deprotection and downstream conversion into free dicarboxylic acid functionality when exposed to acid-labile conditions. The tert-butyl ester groups provide robust stability during peptide coupling and many organic transformations, while the hydrochloride salt form improves handling of the amino acid ester intermediate in synthesis workflows. The resulting reactivity profile supports stepwise assembly of glutamate-containing fragments, preparation of protected peptidic motifs, and conversion into carboxylate-bearing intermediates for biochemical and industrial fine-chemical routes.
1. Peptide Synthesis
L-Glutamic acid di-tert.butyl ester hydrochloride is applied in peptide building-block preparation where glutamate's two carboxyl groups must remain protected during N-terminal or side-chain coupling steps. The di-tert-butyl ester protection pattern allows selective activation of the amino group for amide bond formation while preventing premature hydrolysis of the acidic functionalities that would otherwise interfere with coupling reagents and purification. Acid-labile deprotection can later reveal the free dicarboxylate for incorporation into glutamate-rich sequences or for generating glutamate side-chain functionality in peptide analogs. The protected amino acid ester format supports iterative peptide coupling chemistry and enables downstream conversion to defined glutamate-containing peptide fragments used in research and process-scale peptide intermediate manufacturing.
2. Protected Amino Acid Chemistry
L-Glutamic acid di-tert.butyl ester hydrochloride is used as a chiral, di-carboxylate-protected amino acid intermediate for controlled functional-group management in synthetic organic chemistry. The presence of two tert-butyl ester groups provides orthogonal-like handling relative to other protecting-group strategies, since the esters can be removed under acidic conditions to regenerate the glutamic acid diacid motif. The hydrochloride salt state supports reproducible reagent mixing and can reduce variability associated with free amine handling during protected amino acid synthesis and subsequent transformations. The compound can be employed to generate protected glutamate derivatives for stepwise installation of additional substituents on the side-chain carboxylate after deprotection, supporting targeted amino acid derivatization and intermediate preparation for larger molecular assemblies.
3. Peptidomimetics And SAR Studies
L-Glutamic acid di-tert.butyl ester hydrochloride is suitable for constructing peptidomimetic scaffolds and for structure-activity relationship studies where glutamate's two acidic groups influence binding and conformation. The protected diester form enables incorporation into constrained analogs or linker-bearing fragments without uncontrolled acid-group reactivity during scaffold assembly. Deprotection can be used to expose the dicarboxylate for subsequent derivatization such as salt formation, amide formation, or coupling to electrophiles that install reporter handles or bioisosteric groups. The stereodefined L-glutamate backbone supports consistent stereochemical outcomes across analog libraries, enabling reproducible generation of glutamate-functionalized molecular series for SAR-oriented chemical biology workflows.
4. Bioconjugation Chemistry
L-Glutamic acid di-tert.butyl ester hydrochloride is used in bioconjugation and biomolecule modification schemes where glutamate-derived carboxylate functionality is required for controlled coupling to amine-bearing targets. The di-tert-butyl ester protection helps maintain the carboxyl groups in a masked state during synthesis of conjugation-ready linkers, reducing side reactions from free carboxylates during intermediate assembly. Acid-triggered deprotection can regenerate the dicarboxylate to enable formation of activated ester or amide linkages with biomolecule surfaces, affinity tags, or polymer backbones. The compound's chiral glutamate framework supports consistent linker geometry and can be integrated into conjugation strategies for producing defined glutamate-containing probes and materials used in biochemical research and applied analytical development.
5. Pharmaceutical Intermediate Preparation
L-Glutamic acid di-tert.butyl ester hydrochloride is relevant to pharmaceutical intermediate preparation where protected glutamate motifs serve as precursors for drug-like amide linkers, acidic pharmacophore elements, and metabolically stable analogs. The di-tert-butyl ester protection pattern supports manufacturing-friendly handling by minimizing acid-group participation during key synthetic steps and by enabling later conversion to the free diacid for incorporation into final intermediates. The hydrochloride salt form can facilitate consistent dosing of the amino acid ester in multistep synthesis planning and can reduce variability in downstream coupling chemistry. The compound can be employed to build process chemistry routes toward glutamate-containing intermediates that feed into fine chemical production, including linker synthesis and scaffold elaboration for medicinal chemistry programs.
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