H-Glu(OBzl)-OtBu·HCl is a protected glutamic acid derivative in which the α-amino group is acylated as an N-terminal amide (H-), the side-chain carboxyl is esterified as a benzyl ester (OBzl), and the α-carboxyl is present as a tert-butyl ester (OtBu). The molecule is provided as a hydrochloride salt, pairing the basic functional group with chloride and bearing the glutamate side chain with a γ-carboxyl that is masked as an O-benzyl ester to control chemoselectivity during synthesis. In peptide chemistry and related derivative preparation, this protected amino acid is used as a stepwise building block that suppresses undesired carboxyl reactivity while enabling controlled deprotection and subsequent coupling to form peptide bonds or more complex glutamate-containing intermediates.
CAT No: CP00763
CAS No:105590-97-4
Synonyms/Alias:L-Glutamicacidγ-benzylesterα-tert.butylesterhydrochloride;
H-Glu(OBzl)-OtBu·HCl is a protected glutamic acid derivative in which the α-carboxyl group is present as a tert-butyl ester hydrochloride salt, while the side-chain γ-carboxyl group is benzyl-protected as an OBzl ester. The molecule therefore bears a stereogenic α-carbon characteristic of L-glutamate chemistry, along with a benzylic protecting group that can be removed under hydrogenolysis conditions and a tert-butyl ester that can be cleaved under acidolysis to regenerate the corresponding carboxylic acids. The hydrochloride salt form improves handling of the amino acid ester intermediate by pairing the protected amine environment with chloride, supporting controlled reactivity during peptide coupling and downstream transformations. The combination of orthogonal protection patterns and a glutamate side-chain provides a structurally defined platform for peptide building block preparation, side-chain functionalization, and process-relevant intermediate synthesis.
1. Peptide Synthesis
H-Glu(OBzl)-OtBu·HCl supports peptide coupling workflows by providing a glutamate-based peptide building block with a protected side-chain carboxyl (OBzl) and a protected C-terminal carboxyl (OtBu) that can be selectively activated and transformed. The orthogonal ester protections enable stepwise deprotection strategies, where the tert-butyl ester can be removed to expose the C-terminal carboxylic acid for subsequent coupling, while the benzyl ester can remain intact to preserve side-chain functionality during chain assembly. The α-amino functionality is protected as the N-acylated form implied by the H- prefix, allowing incorporation into peptide sequences using standard amide bond-forming chemistries compatible with amino acid ester intermediates. Glutamate side-chain geometry and stereochemistry help maintain defined residue orientation in peptide analog construction, supporting research-grade synthesis of glutamate-containing peptides and protected fragments.
2. Amino Acid Derivatization
H-Glu(OBzl)-OtBu·HCl is suitable for amino acid derivatization and downstream functional group interconversion because it contains two protected carboxyl groups that can be unmasked in a controlled sequence. The benzyl ester on the γ-carboxyl can be converted to the free acid after hydrogenolysis, enabling side-chain-specific transformations such as activation to mixed anhydrides, conversion to amides, or further elaboration into functional glutamate derivatives. The tert-butyl ester can be removed under acidic conditions to generate a C-terminal carboxyl handle for coupling or for conversion into activated acid derivatives used in fine chemical synthesis. The resulting deprotection-controlled access to both carboxyl termini supports preparation of mono- and di-functional glutamate intermediates used in chemical biology studies, peptide fragment libraries, and process chemistry intermediate streams.
3. Protected Amino Acids
H-Glu(OBzl)-OtBu·HCl functions as a protected amino acid intermediate designed for orthogonally protected glutamic acid chemistry, where benzyl and tert-butyl ester groups provide distinct deprotection windows. The benzyl-protected side-chain carboxyl (OBzl) and tert-butyl-protected C-terminal carboxyl (OtBu) allow selective regeneration of acids without simultaneously disturbing the other ester, supporting controlled synthesis of protected glutamate building blocks for iterative peptide construction. The hydrochloride salt form provides a practical handling profile for chiral amino acid ester intermediates, helping maintain reproducible coupling behavior during manufacturing-relevant synthesis planning. Orthogonal protection patterns also enable selective derivatization at either terminus, supporting preparation of mono-protected glutamate derivatives used for sequence-defined peptide analogs and for scalable intermediate preparation in specialty chemical production.
4. Bioconjugation Chemistry
H-Glu(OBzl)-OtBu·HCl can be applied to bioconjugation chemistry workflows where glutamate-derived linkers or peptide segments require controlled exposure of carboxyl groups for conjugation handles. The side-chain carboxyl protected as OBzl can be unmasked to provide a reactive carboxylate for coupling to amines on biomolecules or to introduce amide-linked tethering motifs, while the C-terminal carboxyl generated from OtBu can serve as a second functional site for orthogonal conjugation strategies. The stereodefined glutamate backbone supports formation of structurally consistent linkers that preserve spatial orientation in protein or peptide conjugates. Downstream use can include preparation of glutamate-containing conjugation fragments for chemical biology research, including labeling reagents, immobilization linkers for affinity materials, and modular components used to assemble biomolecule conjugates.
5. Pharmaceutical Manufacturing
H-Glu(OBzl)-OtBu·HCl is relevant to pharmaceutical manufacturing and process chemistry as a protected glutamic acid intermediate that supports scalable peptide and peptidomimetic synthesis routes. The orthogonal benzyl and tert-butyl ester protection scheme supports manufacturing-friendly sequencing of deprotection and coupling steps, where selective acid liberation can be aligned to process stages for intermediate isolation and purification. The defined stereochemistry of the glutamate α-center helps ensure consistent residue incorporation in peptide intermediates used for downstream synthetic elaboration toward drug-like molecules and analog libraries. The compound's protected-carboxyl functionality enables conversion into activated acid or coupling-ready forms under controlled conditions, supporting fine chemical synthesis operations that require reproducible handling of chiral amino acid derivatives.
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