Boc-L-Glu(Bzl)-ONp is a protected amino acid derivative based on L-glutamic acid bearing a benzyl-protected side-chain carboxyl group (Glu(Bzl)) and an N-terminal Boc (tert-butoxycarbonyl) protecting group. The molecule contains a free α-amino functionality masked by Boc, a carboxyl-derived ONp leaving group (ONp denotes an activated p-nitrophenyl ester), and a benzyl ester on the side-chain carboxyl, giving it two ester carbonyls while controlling chemoselectivity toward acyl transfer at the activated ONp site. As an activated glutamate ester intermediate, it is used in peptide synthesis and related acylation strategies where stepwise coupling of the glutamate residue or incorporation of a glutamate side-chain protected functionality is required for constructing peptide derivatives and conjugates.
CAT No: CP26031
CAS No:7536-59-6
Synonyms/Alias:Boc-Glu(OBzl)-ONp;7536-59-6;AC1Q1MSF;CTK8E9858;MolPort-003-926-650;C23H26N2O8;6359AH;ZINC71788019;AKOS015841412;AKOS015895913;KB-90738;TC-066475;FT-0655371;ST50331303;13974P;I06-1372;Boc-L-Glutamicacid5-benzyl1-(4-nitrophenyl)ester;(4-nitrophenyl)phenylmethyl(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanedioate;4-nitrophenylphenylmethyl(2S)-2-[(tert-butoxy)carbonylamino]pentane-1,5-dioate
Chemical Name:N-alpha-t-Butyloxycarbonyl-L-glutamic acid alpha-(p-nitrophenyl) gamma-benzyl ester
Boc-L-Glu(Bzl)-ONp is a protected glutamic acid derivative featuring an N-terminal Boc group and a benzyl-protected side-chain carboxyl (Bzl), supplied as an ONp ester for activated carboxyl chemistry. This structure is commonly used to prepare glutamate-containing peptide segments and intermediates where controlled acyl transfer is required, with the stereochemistry matching L-glutamate building block workflows. The ONp (p-nitrophenyl) ester form is particularly valued in peptide and intermediate synthesis for enabling efficient coupling under standard amide-forming conditions while maintaining the orthogonal protection pattern needed for multi-step assembly.
1. Peptide Segment Coupling
Boc-L-Glu(Bzl)-ONp is used as an activated glutamate building block in peptide synthesis workflows where glutamic acid residues must be introduced with reliable segment coupling performance. Custom peptide synthesis groups and peptide reagent users rely on the ONp ester to promote acyl transfer to amine partners, supporting the assembly of peptide sequences that require the side-chain carboxyl to remain protected as benzyl during earlier steps. The Boc group at the N-terminus helps maintain compatibility with protected-amino-acid strategies, enabling downstream deprotection and continuation of chain elongation without premature side-chain reactivity.
2. Protected Glutamate Intermediate
Boc-L-Glu(Bzl)-ONp is frequently selected as a pharmaceutical intermediate for preparing glutamate-derived amides and peptide-like linkers that must preserve orthogonal protection during intermediate handling. Process development and medicinal chemistry teams use ONp-activated glutamate derivatives to generate defined acylated intermediates that can be carried forward into solution-phase or convergent synthesis, including the preparation of protected glutamate motifs for larger constructs. The combination of Boc and benzyl side-chain protection supports controlled functional group management, which is especially important when multistep synthesis requires selective deprotection later in the route.
3. Solution-Phase Amide Formation
Boc-L-Glu(Bzl)-ONp supports solution-phase amide bond formation in research and industrial settings where activated esters are preferred for coupling efficiency and operational practicality. Synthetic chemists use the ONp ester to acylate amines under conditions compatible with the Boc/Bzl protection pattern, enabling the preparation of glutamate-containing fragments used in peptide library synthesis, SAR-focused intermediate generation, and linker optimization studies. This reagent format is particularly useful when the target amide must be formed cleanly from a protected glutamate precursor while avoiding side reactions from the unprotected carboxyl groups.
4. Convergent Peptide Assembly
Boc-L-Glu(Bzl)-ONp is applied in convergent peptide assembly strategies where preformed glutamate-containing segments are coupled to complementary fragments to reduce the number of sequential steps. Peptide manufacturing research teams and advanced peptide synthesis laboratories use the ONp activation to facilitate coupling at a defined stage while keeping the side-chain carboxyl protected as Bzl, preserving sequence integrity and minimizing undesired cross-reactivity. The reagent's protected amino acid architecture helps maintain orthogonality across assembly and subsequent deprotection steps, supporting the construction of glutamate-rich peptides and glutamate-functionalized intermediates.
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