Boc-D-Glu(All)-OH is a protected amino acid derivative in which the side chain of D-glutamic acid bears an allyl (All) substituent and the α-amino group is protected as a Boc (tert-butoxycarbonyl) carbamate, making it distinct from an unprotected free amino acid. The molecule contains both an α-carboxylic acid (-COOH) and a Boc-protected amino functionality, while the allyl-bearing side chain provides an alkene handle for orthogonal functionalization or post-synthetic modification; the stereochemistry is specified as D by the product name. In peptide chemistry and chemical biology workflows, this protected analogue is used as a building block for incorporating an allyl-functional glutamate residue under chemoselective protection of the α-amino group, supporting stepwise assembly and subsequent derivatization of the side-chain alkene.
CAT No: CP25678
CAS No:259221-91-5
Synonyms/Alias:259221-91-5;(R)-5-(Allyloxy)-2-((tert-butoxycarbonyl)amino)-5-oxopentanoicacid;BOC-D-GLU(OALL)-OH;Boc-D-glutamicacid-gamma-allylester;AmbotzBAA1032;AC1Q1MU1;CTK8E6912;MolPort-008-267-362;ZINC2386589;2175AB;AKOS015911771;Boc-D-glutamicacidgamma-allylester;AJ-35354;AK115640;AM002990;KB-48272;KB-210217;RT-011732;K-6739;I14-37412;2-tert-Butoxycarbonylamino-pentanedioicacid5-allylester;(2R)-2-[(TERT-BUTOXYCARBONYL)AMINO]-5-OXO-5-(PROP-2-EN-1-YLOXY)PENTANOICACID
Chemical Name:N-alpha-t-Butyloxycarbonyl-D-glutamic acid gamma-allyl ester
Boc-D-Glu(All)-OH is a Boc-protected D-glutamic acid derivative bearing an allyl side-chain protecting group on the glutamate side-chain carboxylate. This stereochemically defined, protected amino acid building block is designed for peptide synthesis workflows where orthogonal side-chain protection is required to control chemoselectivity during assembly and subsequent functionalization. The combination of a Boc N-terminus and an allyl-protected side-chain carboxylate makes it a practical intermediate for preparing glutamate-containing peptides and peptide segments with controlled reactivity.
1. Solid-Phase Peptide Assembly
Boc-D-Glu(All)-OH is used as a protected glutamate building block for solid-phase peptide synthesis, especially when D-glutamate incorporation is required for peptide design, protease studies, or conformational/recognition investigations. The Boc-protected amino group supports controlled coupling as part of peptide segment construction, while the allyl-protected side-chain carboxylate helps prevent undesired side reactions during chain elongation. Researchers assembling D-amino-acid-containing peptides commonly select this type of side-chain protection to maintain the glutamate functionality in a protected, non-interfering form until the peptide is ready for downstream modification.
2. Orthogonal Side-Chain Deprotection
Boc-D-Glu(All)-OH supports workflows that require selective unveiling of the glutamate side-chain for late-stage derivatization after peptide assembly. The allyl side-chain protection enables chemoselective manipulation distinct from the N-terminal Boc group, which is valuable in peptide development programs where the timing of functional group exposure affects labeling efficiency, conjugation compatibility, or subsequent coupling steps. Chemical biology teams and peptide synthesis groups often rely on this orthogonal protection strategy to generate glutamate-bearing peptides for further attachment to linkers, tags, or other biomolecular components while keeping the remainder of the sequence protected during earlier steps.
3. Peptide Conjugation Precursors
Boc-D-Glu(All)-OH is frequently incorporated into peptide intermediates intended for preparation of glutamate-functional peptide conjugates, including peptide-linker constructs used in assay development and biomaterials research. By carrying a protected glutamate side-chain during synthesis, the building block helps ensure that conjugation-ready functionality is introduced only after the peptide backbone is assembled and purified. This approach is particularly useful when the final conjugate requires controlled stoichiometry and minimized side reactions, since the allyl-protected carboxylate can be converted to the corresponding reactive carboxylate form at the appropriate stage of the workflow.
4. D-Amino-Acid Peptide Studies
Boc-D-Glu(All)-OH is used by researchers designing peptides with D-amino-acid content to probe structure-property relationships and sequence-dependent behavior in chemical biology and protein-interaction studies. The defined D-stereochemistry at the glutamate residue is valuable for generating peptide variants that differ stereochemically from their L counterparts, enabling systematic comparisons in binding studies, stability-focused experiments, and mechanistic investigations using peptide analogs. In these projects, the protected form is essential to reliably synthesize full-length or segmental D-glutamate-containing peptides while preserving the side-chain functionality for later modification or for maintaining it in a defined state throughout the study.
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