Boc-Glu(OSu)-OBzl is a protected glutamic acid derivative featuring an N-terminal Boc (tert-butoxycarbonyl) protecting group and a C-terminal benzyl ester (OBzl) on the amino acid backbone. The side chain is present as a glutamate N-hydroxysuccinimide ester (OSu), providing an activated carboxyl functionality for amide bond formation, while the molecule retains the amino and carboxyl connectivity characteristic of glutamate. This compound is used in peptide chemistry and bioconjugation workflows as an electrophilic amino-acid building block that can be coupled to nucleophiles to generate glutamate-containing linkages under conditions compatible with Boc and benzyl ester protection.
CAT No: CP27476
CAS No:78658-49-8
Synonyms/Alias:BOC-GLU(OSU)-OBZL;78658-49-8;BOC-GLU-OBZL;6362AH;KM1929;ZINC71788026;AKOS025289409;AK170149;N-(tert-Butoxycarbonyl)-L-glutamicacid1-benzyl5-succinimidylester
Boc-Glu(OSu)-OBzl is a protected glutamic acid derivative designed for peptide and amide bond formation, featuring a Boc-protected alpha-amino group and a side-chain activated ester (OSu) alongside a benzyl ester (OBzl). This combination supports controlled coupling chemistry in peptide assembly workflows while maintaining orthogonal protection patterns that are commonly leveraged to build glutamate-containing sequences and related intermediates. Researchers use this reagent to access glutamate side-chain functionality in a protected, reactive form suitable for stepwise synthesis and downstream conversion to defined peptide or peptidomimetic structures.
1. Glutamate Side-Chain Coupling
Boc-Glu(OSu)-OBzl is used in peptide synthesis workflows where glutamate side-chain activation is required to promote efficient coupling during segment assembly or late-stage functionalization. In custom peptide manufacturing and medicinal chemistry programs, peptide chemists select this activated glutamate derivative to introduce a protected glutamate unit with a defined side-chain reactivity handle, enabling controlled formation of amide linkages while keeping the alpha-amino functionality protected for sequential assembly. The OSu activation is particularly relevant when the downstream partner is an amino component that benefits from activated ester chemistry, supporting consistent incorporation of glutamate residues into peptides and peptidomimetics.
2. Protected Intermediate For Peptidomimetics
Boc-Glu(OSu)-OBzl serves as a practical building block for synthesizing glutamate-containing peptidomimetic scaffolds and protected intermediates used in structure-activity relationship (SAR) studies. Medicinal chemistry groups often rely on activated, protected amino acid derivatives to generate well-defined intermediates that can be carried forward into library synthesis, fragment coupling, or solution-phase assembly of complex amide-rich molecules. The presence of Boc and OBzl protection helps maintain chemoselectivity across multi-step sequences, allowing the reagent to be used as a glutamate source that preserves the intended protection pattern until the intermediate is advanced to the next synthetic stage.
3. Stepwise Peptide Segment Assembly
Boc-Glu(OSu)-OBzl is applied in stepwise peptide segment construction where glutamate residues must be incorporated with reliable protection and coupling behavior. Peptide synthesis teams use this reagent to prepare glutamate-bearing segments or to perform targeted couplings that require a side-chain activated ester, helping reduce variability associated with side-chain functional group handling in multi-residue sequences. The protected architecture supports workflow compatibility in both academic peptide chemistry and industrial peptide development settings, where reproducible intermediate generation is essential for assembling peptides with defined glutamate positioning and protected termini.
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