Boc-Glu(OMe)-ONp is a protected glutamic acid derivative in which the α-amino group is masked as a Boc carbamate and the side-chain carboxyl group is methylated (Glu(OMe)), forming a glutamate-based building block for peptide-related chemistry. The molecule bears a free α-carboxylate equivalent and an O-methyl ester side-chain, and the ONp group (p-nitrophenyl ester) provides an activated carboxylate functionality that can undergo acyl transfer under appropriate conditions while maintaining the Boc-protected amino group for chemoselective coupling. Boc-Glu(OMe)-ONp is used as a reagent for constructing peptide bonds and for preparing glutamate-containing peptide intermediates, including steps where controlled activation of a carboxyl group is required for subsequent amide formation.
CAT No: CP26486
CAS No:16947-07-2
Synonyms/Alias:BOC-GLU(OME)-ONP;16947-07-2;CTK8F8288;C17H22N2O8;ZINC2556543;6361AH;AKOS022181184;AK-60181;K-5236;Boc-L-glutamicacidgamma-methylesteralpha-4-nitrophenylester;(S)-5-Methyl1-(4-nitrophenyl)2-((tert-butoxycarbonyl)amino)pentanedioate
Boc-Glu(OMe)-ONp is a Boc-protected glutamate derivative bearing a methyl ester on the side chain and an o-nitrophenyl (ONp) ester at the activated carboxylate position, providing an amino-acid building block designed for efficient peptide coupling. The glutamate stereochemistry is maintained from the starting material and the combination of Boc protection with an activated ONp ester makes this reagent a practical intermediate for assembling protected peptide segments under standard peptide synthesis conditions. Researchers commonly select this specific activation/ester pattern when they need a glutamate residue with controlled functional-group masking for downstream deprotection and fragment condensation.
1. Peptide Segment Coupling
Boc-Glu(OMe)-ONp is used as an activated glutamate building block for peptide synthesis workflows that rely on pre-activated amino-acid esters to promote fragment condensation. Peptide chemistry groups preparing protected peptide intermediates often prefer the ONp-activated carboxylate because it supports coupling to appropriately protected amines while keeping the side-chain functionality masked as a methyl ester, which helps maintain compatibility with subsequent steps. This format is frequently chosen for assembling glutamate-containing sequences where the N-terminus remains Boc-protected during segment assembly, supporting controlled deprotection planning in multi-step syntheses.
2. Protected Glutamate Intermediate
Boc-Glu(OMe)-ONp serves as a glutamate-specific intermediate for downstream synthesis of peptides and peptide-like molecules that require a methyl-ester side chain during early stages. Medicinal chemistry and peptide development teams use this reagent to introduce a glutamate residue with a defined side-chain protection state, allowing controlled conversion of the side-chain ester at a later stage when the synthetic route reaches the desired functionalization point. The Boc group and methyl ester combination are particularly useful when the synthetic strategy requires orthogonal timing of deprotection or functional-group manipulation, enabling efficient progression from protected fragments to more elaborated peptide structures.
3. Solution-Phase Fragment Synthesis
Boc-Glu(OMe)-ONp is frequently deployed in solution-phase peptide synthesis and custom peptide manufacturing research where activated amino-acid esters are used to couple fragments without requiring solid support. Chemical synthesis teams value this reagent for its defined activated ester handle, which can improve operational efficiency when building longer, protected peptide segments or when preparing difficult-to-handle sequences that benefit from solution-phase control. By maintaining the glutamate side chain as a methyl ester and the amino terminus as Boc-protected, the reagent supports a consistent protecting-group environment throughout coupling and subsequent purification steps.
4. Pharmaceutical Peptide Intermediate Development
Boc-Glu(OMe)-ONp is also used in the preparation of protected peptide intermediates for pharmaceutical and bioconjugation-related development programs, where glutamate residues must be introduced with predictable functional-group protection. Process development chemists and peptide R&D groups often select this activated, Boc-protected glutamate ester form to streamline the synthesis of key intermediates used in library production, analog generation, or final-stage functionalization. The reagent's protected-state design helps ensure that the glutamate side chain does not interfere with earlier coupling chemistry, supporting reliable intermediate handling during iterative synthesis and characterization workflows.
1. An Open-label, Single-center, Safety and Efficacy Study of Eyelash Polygrowth Factor Serum
4. Emerging applications of nanotechnology for diagnosis and therapy of disease: a review
If you have any peptide synthesis requirement in mind, please do not hesitate to contact us at . We will endeavor to provide highly satisfying products and services.
Creative Peptides is a trusted CDMO partner specializing in high-quality peptide synthesis, conjugation, and manufacturing under strict cGMP compliance. With advanced technology platforms and a team of experienced scientists, we deliver tailored peptide solutions to support drug discovery, clinical development, and cosmetic innovation worldwide.
From custom peptide synthesis to complex peptide-drug conjugates, we provide flexible, end-to-end services designed to accelerate timelines and ensure regulatory excellence. Our commitment to quality, reliability, and innovation has made us a preferred partner across the pharmaceutical, biotechnology, and personal care industries.
Read More