Boc-Glu(OcHex)-OH is a protected glutamic acid derivative in which the α-amino group is masked as a Boc (tert-butoxycarbonyl) carbamate and the side-chain γ-carboxyl group is esterified as an OcHex (cyclohexyl ester) functionality. The molecule therefore contains a Boc-protected amino terminus and two carboxyl-derived groups, with the side-chain carboxyl converted to a cyclohexyl ester that modulates polarity and prevents side-chain carboxyl reactivity during peptide coupling. In peptide chemistry, this protected amino acid is used as a building block for stepwise assembly where chemoselective activation of the α-carboxyl and controlled handling of the side-chain carboxyl are required for constructing glutamate-containing sequences.
CAT No: CP27412
CAS No:73821-97-3
Synonyms/Alias:Boc-Glu(OcHex)-OH;73821-97-3;Boc-Glu(OcHx)-OH;(S)-2-((tert-Butoxycarbonyl)amino)-5-(cyclohexyloxy)-5-oxopentanoicacid;Boc-L-glutamicacid5-cyclohexylester;N-(tert-Butoxycarbonyl)-L-glutamicAcid5-CyclohexylEster;Boc-L-glutamicacidgamma-cyclohexylester;Boc-Glu(OcHx);PubChem12179;15437_ALDRICH;15437_FLUKA;EBD2665;MolPort-003-926-794;ACT08692;ZINC2539203;Boc-L-Glutamicacid-5-cyclohexylester;CB-334;KM1572;SBB065832;AKOS015892687;AKOS015924144;AJ-38808;AK-45994;KB-48299;N-Boc-L-glutamicAcid5-CyclohexylEster
Boc-Glu(OcHex)-OH is a Boc-protected glutamic acid derivative featuring an OcHex ester on the side-chain carboxyl group, providing controlled reactivity and compatibility with protected-amino-acid peptide assembly workflows. This protected amino acid building block is commonly used to introduce glutamate residues while minimizing side-chain interference during coupling and deprotection steps, making it a practical choice for preparing glutamate-containing peptides and peptide-based intermediates. The combination of N-terminal Boc protection and side-chain carboxyl esterification supports sequential synthetic strategies used in custom peptide manufacturing and medicinal chemistry programs.
1. Solid-Phase Peptide Synthesis
Boc-Glu(OcHex)-OH is used by peptide synthesis groups to incorporate glutamate residues into peptide sequences during solid-phase peptide synthesis, where orthogonal protection and stepwise deprotection are essential for sequence fidelity. The Boc group on the amino terminus supports standard N-protection strategies in iterative chain assembly, while the OcHex side-chain ester helps suppress undesired side reactions from the glutamate side-chain carboxyl during coupling cycles. This makes the building block useful for preparing protected peptide segments that later undergo controlled side-chain unveiling for downstream functionalization or final peptide generation.
2. Glutamate Side-Chain Functionalization
Boc-Glu(OcHex)-OH is selected in medicinal chemistry and peptide chemistry workflows that require glutamate side-chain availability after peptide assembly, such as generating peptides for subsequent conjugation, derivatization, or incorporation into larger constructs. By keeping the side-chain carboxyl esterified during early stages, the reagent supports cleaner peptide synthesis and reduces competing reactivity, while enabling later conversion of the glutamate side-chain into a reactive carboxylate for coupling chemistry. Researchers commonly use this approach when designing glutamate-containing intermediates that must tolerate multiple synthetic operations before final side-chain activation.
3. Pharmaceutical Intermediate Development
Boc-Glu(OcHex)-OH is also used as a protected glutamate building block for preparing peptide-based pharmaceutical intermediates, including protected fragments used in solution-phase segment coupling and late-stage assembly. The controlled protection pattern helps manage chemoselectivity across multistep sequences where both amide bond formation and selective deprotection are required to reach the desired intermediate profile. Process and development chemists value this protected form for producing glutamate-containing intermediates with reduced side-chain reactivity during handling, purification, and coupling steps, supporting reliable downstream conversion to target peptide scaffolds.
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