Boc-Glu(Ome)-OH·DCHA 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 present as a methyl ester (Glu(Ome)). The molecule contains a Boc-protected amine together with a free carboxylic acid at the α-position, and the DCHA counterion indicates formation of a salt that can influence crystallinity and handling while preserving the protected functionality. In peptide and amino-acid derivative synthesis, this compound serves as a stepwise building block for introducing a glutamate unit with a protected side-chain carboxyl group, supporting controlled chemoselectivity during coupling and subsequent deprotection strategies.
CAT No: CP00718
CAS No:14406-17-8
Synonyms/Alias:Boc-L-glutamicacid γ-methyl esterdicyclohexylamine salt;14406-17-8;BOC-GLU(OME)-OHDCHA;Dicyclohexylamine(S)-2-((tert-butoxycarbonyl)amino)-5-methoxy-5-oxopentanoate;Boc-Glu-Ome.DCHA;PubChem12015;Boc-Glu(OMe)-OHCHA;Boc-Glu(OMe)-OH.DCHA;CTK0H3984;Boc-Glu(OMe)-OH?currencyDCHA;MolPort-003-983-021;CB-335;AKOS015840977;AKOS016002262;AK-49399;KB-90810;TC-066728;FT-0654684;K-4618;Boc-L-Glutamicacid-gamma-methylesterdchasalt;Q-101683;L-Glutamicacid,N-[(1,1-dimethylethoxy)carbonyl]-,5-methylester,compd.withN-cyclohexylcyclohexanamine(1:1)
Boc-Glu(Ome)-OH·DCHA is a Boc-protected glutamic acid derivative bearing a methyl ester on the side-chain (Glu(Ome)) and provided as a dicyclohexylamine (DCHA) salt, which improves handling and facilitates consistent dosing in peptide synthesis workflows. The combination of a Boc-protected alpha-amino group and an esterified side chain makes this building block well-suited for controlled assembly of glutamate-containing peptide segments and for downstream functionalization steps where temporary masking of the side-chain carboxyl is required.
1. Fmoc-Free Peptide Segment Building
Boc-Glu(Ome)-OH·DCHA is used by custom peptide synthesis groups and peptide manufacturing teams to construct glutamate-containing sequences via Boc-based strategies, where the alpha-amino group is protected as a Boc carbamate. The side-chain methyl ester (Ome) provides a protected glutamate functionality during segment coupling, helping maintain chemoselectivity during iterative chain assembly. This format is particularly valuable when a synthesis plan requires keeping the glutamate side chain masked until later stages, such as during solution-phase segment condensation or when assembling longer peptide intermediates that must tolerate multiple coupling and deprotection operations.
2. Protected Glutamate Intermediate Synthesis
Boc-Glu(Ome)-OH·DCHA is widely applied in medicinal chemistry and pharmaceutical intermediate development to generate glutamate-derived protected intermediates for subsequent elaboration. By carrying both an alpha-amino protecting group (Boc) and a side-chain carboxyl masking group (methyl ester), the reagent supports stepwise downstream transformations while limiting side reactions associated with free carboxylic acids. Process chemists and heteropeptide developers often select this protected form to standardize intermediate quality across batches, enabling reproducible conversion into activated glutamate derivatives or into peptide-ready building blocks used in library synthesis and analog preparation.
3. Glutamate Side-Chain Masking Control
Boc-Glu(Ome)-OH·DCHA supports workflows that require precise control over when the glutamate side-chain carboxyl functionality is revealed. In peptide and peptidomimetic development, the methyl ester on the side chain acts as a temporary protecting group that can be removed or transformed at a chosen stage, allowing the synthesis team to manage compatibility with other functional groups present in the growing scaffold. Researchers building glutamate-rich motifs, including polar or charge-dense peptide segments, often prefer this protected glutamate format to reduce undesired aggregation or reactivity during assembly, while still retaining a clear path to generate the corresponding free carboxyl for later coupling, conjugation, or final deprotection steps.
4. Analytical Reference for Boc-Glutamate Chemistry
Boc-Glu(Ome)-OH·DCHA is also used as a reference material in analytical method development and characterization of Boc-protected glutamate intermediates. Peptide chemistry laboratories and contract research organizations employ this compound to verify identity and retention behavior in routine HPLC/UPLC workflows and to support method qualification when monitoring protected amino acid incorporation and intermediate purity. The defined protection pattern (Boc on the alpha-amino group and methyl ester on the side chain) makes it a practical standard for tracking protected-state conversions during peptide synthesis and for confirming the presence of glutamate-derived building blocks in intermediate mixtures.
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