Boc-D-His(3-Me)-OH is a Boc-protected, D-configured histidine derivative in which the imidazole side chain bears a 3-methyl substituent, making it a non-unmodified amino acid building block for peptide-related synthesis. The molecule contains a carboxylic acid and an amino group masked as a Boc carbamate, while the substituted imidazole provides a basic, hydrogen-bonding side-chain functionality that can influence coordination and interaction patterns in assembled peptides. In synthetic workflows, this protected amino acid is employed to introduce the sterically and electronically modified histidine residue into peptide chains under conditions that rely on the Boc group to control chemoselectivity during stepwise coupling.
CAT No: CP26670
CAS No:200871-84-7
Synonyms/Alias:BOC-D-HIS(3-ME)-OH;200871-84-7;AC1OLRG2;Boc-D-His(pi-Me)-OH;SCHEMBL7052233;CTK8F0142;6329AH;ZINC36208751;RT-011734;(2R)-3-(3-methylimidazol-4-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoicacid
Boc-D-His(3-Me)-OH is a protected, D-configured histidine derivative bearing a Boc-protected amino group and a 3-methyl substituted imidazole side chain. This stereochemically defined amino acid building block is used in peptide chemistry when a histidine-like residue with altered side-chain substitution is needed to probe structure, control local reactivity, or tune physicochemical behavior in synthetic sequences. The protected form supports routine incorporation into protected-peptide intermediates via standard peptide assembly workflows.
1. Modified Peptide Building Block
Boc-D-His(3-Me)-OH is used by peptide chemists to introduce a D-histidine analogue with a 3-methylated imidazole side chain into custom peptide targets. Researchers commonly select this residue to modulate histidine side-chain properties relative to unsubstituted histidine, supporting studies where side-chain substitution, steric profile, or imidazole microenvironment is expected to influence folding, conformation, or local interactions. The Boc protection at the α-amino position enables its use as a defined amino acid component in stepwise peptide synthesis and in the preparation of protected peptide segments for subsequent coupling.
2. Peptide Library And SAR Studies
Boc-D-His(3-Me)-OH is frequently incorporated into small-molecule-like peptide libraries and structure-activity relationship (SAR) campaigns where noncanonical histidine analogues are used to map sequence features to function. Medicinal chemistry groups and peptide discovery teams employ this building block to systematically vary side-chain substitution patterns while keeping the backbone residue identity consistent across analog series. The D-configuration and 3-Me imidazole substitution provide a practical handle for generating stereochemically and electronically distinct peptide variants, which are then evaluated in downstream biochemical or biophysical assays developed by the same teams.
3. Protected Intermediate For Custom Synthesis
Boc-D-His(3-Me)-OH serves as a reliable protected amino acid intermediate for the manufacturing of peptide fragments and advanced intermediates used in custom peptide synthesis. Process development and synthetic chemistry teams use Boc-protected amino acid building blocks to maintain compatibility with protected-peptide handling, enabling controlled assembly of longer sequences through iterative coupling steps. Because the side chain is pre-functionalized with the 3-methyl group, the residue can be introduced as a single, well-defined component rather than relying on post-assembly side-chain modification, which supports efficient route design for complex peptide architectures.
4. Stereochemical Control In Peptide Design
Boc-D-His(3-Me)-OH is used in peptide design workflows that require explicit stereochemical control at the residue level, particularly when D-amino acid content is leveraged to influence peptide conformation and stability profiles during research development. Protein engineering and chemical biology groups may include D-configured residues to create peptides with altered backbone stereochemistry while retaining a histidine-like side-chain motif for interaction mapping. The combination of Boc protection and a 3-methyl imidazole substitution supports the synthesis of well-defined analogs for mechanistic studies, binding-interface probing, and structure-guided refinement of peptide leads.
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