Boc-L-His(1-Me)-OH is a protected, naturally derived amino acid derivative featuring the histidine backbone bearing an N-methyl substitution at the imidazole ring position (1-methylhistidine) and an Nα-Boc protecting group. The molecule contains a free carboxylic acid and a Boc-protected amino group, while the N-methylated imidazole side chain alters hydrogen-bonding and basicity compared with unmodified histidine and provides a defined aromatic heterocycle for controlled side-chain behavior. In peptide synthesis and related chemical biology workflows, this compound functions as a stepwise building block that supports chemoselective coupling of the protected amino acid while retaining a substituted histidine-like side chain for incorporation into peptides or for preparing more complex amino acid derivatives.
CAT No: CP25935
CAS No:61070-20-0
Synonyms/Alias:Bz-Glu-OH;6094-36-6;N-Benzoyl-L-glutamicacid;(S)-2-Benzamidopentanedioicacid;Benzoyl-L-glutamicacid;(2S)-2-(phenylformamido)pentanedioicacid;UNII-3591D74MXP;LPJXPACOXRZCCP-VIFPVBQESA-N;3591D74MXP;SBB008417;N-Benzoylglutamicacid;(2S)-2-(phenylcarbonylamino)pentanedioicacid;N-Benzoylglutamicacid#;L-Glutamicacid,N-benzoyl-;SCHEMBL97498;N-benzoyl-(S)-glutamicacid;CHEMBL22546;AC1Q74U9;CTK3J1673;Glutamicacid,N-benzoyl-,L-;MolPort-001-840-350;(S)-(+)-N-Benzoylglutamicacid;(S)-(-)-N-benzoylglutamicacid;58094-18-1;ZINC1624515
Chemical Name:N-alpha-t-Butyloxycarbonyl-1-methyl-L-histidine
Boc-L-His(1-Me)-OH is a Boc-protected histidine derivative bearing an N1-methylated imidazole side chain, provided as a protected amino acid building block for peptide and peptidomimetic synthesis. The Nα is protected with a Boc group, while the side-chain imidazole is substituted at the 1-position, which helps tune basicity and side-chain reactivity during stepwise assembly. This protected, stereochemically defined amino acid is widely used in research settings where controlled incorporation of modified histidine residues is required to probe structure-property relationships or generate defined peptide intermediates.
1. Peptide Synthesis Building Block
Boc-L-His(1-Me)-OH is used by peptide chemistry groups to assemble peptides containing a 1-methylated histidine residue, enabling defined side-chain substitution patterns that are difficult to achieve with unmodified histidine. The Boc protection at the amino terminus supports its role as a protected amino acid building block for segment coupling workflows, while the N1-methylated imidazole provides a distinct electronic and protonation profile compared with native histidine. Custom peptide synthesis providers and academic labs commonly select this reagent when preparing peptides for downstream biological assays, binding studies, or mechanistic experiments that require a specific histidine analog rather than a generic histidine residue.
2. Peptidomimetic And Analog Design
Boc-L-His(1-Me)-OH supports medicinal chemistry and chemical biology programs focused on peptidomimetic design, where histidine side chains are modified to adjust local charge distribution, hydrogen-bonding patterns, and conformational preferences within peptide scaffolds. Researchers use this building block to generate analog series that systematically vary histidine substitution, improving interpretability of structure-activity or structure-property trends in peptide-based leads. Because the reagent is already protected and stereochemically specified, it fits cleanly into iterative analog-building campaigns where consistent residue identity and reproducible coupling outcomes are essential for comparing multiple peptide variants.
3. Defined Histidine Analog Intermediates
Boc-L-His(1-Me)-OH is also employed to prepare well-defined peptide fragments and protected intermediates used in larger synthesis campaigns, including stepwise assembly of longer sequences or modular construction of peptide domains. In these workflows, the Boc-protected N-terminus and the N1-methylated imidazole side chain help ensure that the residue identity remains consistent across intermediate purification and subsequent coupling steps. Pharmaceutical intermediate development teams and peptide manufacturing research groups rely on such protected amino acid derivatives to minimize ambiguity in residue composition when producing reference materials for method development, analytical characterization, or internal benchmarking of peptide synthesis routes.
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