Boc-D-Glu(OtBu)-OH is a protected amino acid derivative of D-glutamic acid, featuring a Boc-protected amino group and a side-chain γ-carboxyl protected as a tert-butyl ester. The molecule contains a free carboxylic acid at the α-position, while the stereochemical configuration is specified as D and the γ-carboxyl functionality is masked by the OtBu group to reduce undesired carboxyl reactivity during coupling. In peptide chemistry, this orthogonally protected glutamate analogue is used as a building block in stepwise synthesis to support controlled formation of peptide bonds while deferring side-chain deprotection until later stages of derivative preparation.
CAT No: CP26157
CAS No:104719-63-3
Synonyms/Alias:Boc-D-Glu(OtBu)-OH;104719-63-3;Boc-D-glutamicacid5-tert-butylester;(R)-5-(tert-Butoxy)-2-((tert-butoxycarbonyl)amino)-5-oxopentanoicacid;D-Glutamicacid,N-[(1,1-dimethylethoxy)carbonyl]-,5-(1,1-dimethylethyl)ester;15113_ALDRICH;SCHEMBL2564729;15113_FLUKA;MolPort-003-926-652;YGSRAYJBEREVRB-SECBINFHSA-N;ZINC2555000;AKOS015893006;CB-1671;AC-19267;AJ-39665;AK-49224;TR-001027;FT-0657311;FT-0686529;ST24035504;Z6755;B-6329;I04-1550;J-300113;Q-101803
Boc-D-Glu(OtBu)-OH is a protected glutamic acid building block featuring a Boc-protected alpha-amino group and an OtBu-protected side-chain carboxylate, supplied as the D-stereoisomer. This combination of orthogonally protected functionalities makes it a practical reagent for assembling glutamate-containing peptides and peptide segments where stereochemical control and side-chain protection are required. The protected carboxylate enables reliable peptide coupling without premature side-chain reactivity during chain elongation.
1. D-Glutamate Peptide Synthesis
Boc-D-Glu(OtBu)-OH is used by peptide synthesis groups to incorporate D-glutamate residues into solution-phase or protected-segment workflows, providing a protected side-chain that remains inert to coupling conditions. Researchers preparing D-amino-acid enriched peptides rely on this reagent to control stereochemistry at the glutamate position while maintaining the side-chain carboxylate as an OtBu-protected ester during assembly. The Boc group supports standard peptide-building strategies that require temporary N-terminal protection, while the OtBu side-chain protection helps prevent side reactions such as side-chain participation or uncontrolled branching during chain elongation.
2. Stereocontrolled Peptidomimetic Design
Boc-D-Glu(OtBu)-OH supports medicinal chemistry and chemical biology programs that develop peptidomimetics or constrained peptide analogs containing D-glutamate motifs. Teams exploring structure-property relationships often select D-configured glutamate to modulate backbone geometry and resistance to enzymatic processing in downstream studies, while the protected side-chain ensures clean incorporation into longer sequences. The reagent's protected carboxylate functionality is particularly useful when the final free side-chain is needed only after peptide assembly and deprotection, enabling late-stage unveiling of the acidic functionality for subsequent conjugation, salt formation, or further derivatization.
3. Pharmaceutical Intermediate Building Block
Boc-D-Glu(OtBu)-OH is frequently employed in pharmaceutical intermediate development where D-glutamate-containing fragments must be synthesized with robust protection to survive multi-step coupling and purification sequences. Process chemistry teams use this protected amino acid to prepare defined glutamate units for later conversion into activated derivatives, peptide-like intermediates, or protected glutamate-containing scaffolds. The Boc and OtBu protection pattern provides practical handling stability during intermediate manufacturing, while preserving the ability to generate the corresponding D-glutamate functionality in a controlled manner after the final deprotection step.
4. Protected Segment Coupling
Boc-D-Glu(OtBu)-OH is used in custom peptide manufacturing and research-scale segment condensation to build longer sequences from pre-assembled fragments that require consistent protection chemistry. Peptide chemists value the reagent for its protected alpha-amino and side-chain carboxylate, which helps maintain compatibility with protected peptide intermediates and reduces the risk of side-chain interference during condensation. This makes it a common choice when assembling glutamate-containing segments that will later be fully deprotected to yield the desired D-glutamate residues in the final peptide product.
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