Boc-His-OMe is a protected histidine derivative in which the imidazole-containing side chain of histidine is retained while the amino group is masked as a Boc (tert-butoxycarbonyl) carbamate and the carboxyl group is converted to a methyl ester (OMe). The molecule therefore bears a Boc-protected α-amino functionality and an esterified C-terminus, with the histidine imidazole ring providing pH-dependent basicity and a site for coordination and side-chain functionalization in peptide contexts. As a stepwise peptide-synthesis intermediate, it is used to control chemoselectivity of the α-amino group during coupling and to furnish a protected, ester-terminated histidine building block for constructing histidine-containing peptides and related amino acid derivatives.
CAT No: CP26861
CAS No:2488-14-4
Synonyms/Alias:BOC-HIS-OME;2488-14-4;Nalpha-Boc-L-histidinemethylester;(S)-Methyl2-((tert-butoxycarbonyl)amino)-3-(1H-imidazol-5-yl)propanoate;N-Boc-L-histidinemethylester;SCHEMBL1486139;CTK8G1607;MolPort-020-003-858;RWEVEEORUORBAX-VIFPVBQESA-N;ZINC2534423;6369AH;AKOS025286038;AK166996;FT-0698091;K-6598;N-(tert-butoxycarbonyl)-L-histidinemethylester;L-Histidine,N-[(1,1-dimethylethoxy)carbonyl]-,methylester;(S)-methyl2-((tert-butoxycarbonyl)amino)-3-(1H-imidazol-4-yl)propanoate;methyl(2S)-2-[(tert-butoxycarbonyl)amino]-3-(1H-imidazol-4-yl)propanoate
Boc-His-OMe is a protected histidine derivative featuring an N-terminal Boc (tert-butoxycarbonyl) group and a methyl ester at the C-terminus, providing a stable, masked form of both the α-amino functionality and the carboxylate for controlled peptide assembly. The histidine side chain remains available for downstream coupling and orthogonal reactivity management during segment condensation and peptide library workflows, making this building block a common choice in synthetic peptide chemistry where defined termini are required.
1. Solid-Phase Peptide Segments
Boc-His-OMe is frequently used to prepare histidine-containing peptide segments where a protected amino acid unit with a defined C-terminal methyl ester supports efficient downstream transformations during custom peptide synthesis. Peptide synthesis teams value the Boc-protected α-amino group for compatibility with standard deprotection/coupling cycles, while the esterified carboxyl end helps maintain segment integrity prior to final conversion to the target peptide format. This form is particularly relevant when histidine residues must be introduced into sequences that will later undergo additional functionalization steps or careful purification, such as in research-grade peptide standards and structure-activity relationship (SAR) libraries.
2. Solution-Phase Peptide Assembly
Boc-His-OMe is also applied in solution-phase peptide synthesis workflows for constructing defined oligopeptides and intermediate fragments that require a stable, protected histidine building block. In these workflows, the combination of N-Boc protection and C-terminal ester masking helps reduce side reactions associated with free amine or carboxylate groups, enabling more controlled coupling and purification of intermediate fragments. Medicinal chemistry groups and peptide development laboratories often select this derivative when they need a histidine unit that can be incorporated into larger constructs before final ester-to-amide conversion or terminal adjustments for the intended peptide format.
3. Histidine-Containing Intermediate Development
Boc-His-OMe is well suited for pharmaceutical intermediate development and peptide-manufacturing research where histidine-bearing intermediates must be handled as discrete, isolable units. The protected termini simplify material handling and allow stepwise assembly of complex sequences, including fragments used for later ligation, derivatization, or conversion into final peptide products. This derivative is commonly chosen when a controlled histidine incorporation strategy is required to support downstream process development, such as preparing sequence-defined intermediates for custom peptide synthesis, analytical reference peptides, and iterative library build-outs in discovery chemistry programs.
4. Peptide Library and SAR Building Blocks
Boc-His-OMe is widely used in peptide library construction and SAR studies that require rapid, reliable incorporation of histidine residues into multiple sequence variants. Research groups benefit from the consistent protected functionality of this building block, which supports parallel synthesis of histidine-containing analogs while maintaining a predictable intermediate profile for coupling and purification. By using Boc-protected, C-esterified histidine units, peptide chemists can streamline the assembly of analog panels used to probe structure-activity relationships, generate sequence-defined standards for characterization, and support iterative optimization of peptide leads in chemical biology and medicinal chemistry settings.
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