Boc-His(3-Bom)-OSu is a Boc-protected histidine derivative bearing a 3-bromomethyl substituent on the imidazole ring and an N-hydroxysuccinimide (OSu) ester at the carboxyl terminus. The molecule contains a tert-butoxycarbonyl (Boc) protecting group on the amino functionality, while the carboxyl group is activated as an OSu ester for acyl transfer chemistry and the bromomethyl side chain provides a reactive electrophile for subsequent derivatization. In peptide and bioconjugation workflows, this protected amino acid OSu ester is used as a stepwise coupling precursor or as an activated building block to introduce a histidine-like residue with a functional handle for labeling, crosslinking, or side-chain modification studies.
CAT No: CP26295
CAS No:129672-10-2
Synonyms/Alias:129672-10-2;Boc-His(pi-Bom)-OSu;Boc-His(3-Bom)-Osu;6366AH;ZINC71788028
Boc-His(3-Bom)-OSu is a protected histidine derivative bearing a Boc-protected alpha-amino group and a side-chain 3-bromomethyl substituent, supplied as an N-hydroxysuccinimide (OSu) ester. This activated ester format is designed for efficient coupling in peptide and bioconjugation workflows, while the bromomethyl functionality provides a chemically handle for subsequent derivatization. The combination of controlled protection (Boc) and an OSu leaving group supports stepwise assembly of protected peptide fragments and downstream functionalization strategies in chemical biology and medicinal chemistry research.
1. Peptide Fragment Coupling
Boc-His(3-Bom)-OSu is used as an activated amino acid building block for peptide synthesis where an OSu ester enables efficient amide bond formation during segment condensation or solution-phase coupling. Research groups developing protected peptide intermediates commonly select this derivative to introduce a histidine residue bearing a side-chain bromomethyl handle, allowing the side chain to remain masked during coupling and then be carried forward as a functional group for later steps. The Boc protection on the alpha-amino group supports controlled reactivity across multi-step assembly, which is especially valuable when preparing complex peptide sequences or peptide conjugates that require orthogonal downstream modifications.
2. Side-Chain Functionalization Handles
Boc-His(3-Bom)-OSu is frequently chosen when a histidine side chain needs to be carried into a target molecule with a reactive bromomethyl group for subsequent nucleophilic substitution or alkylation chemistry. Chemical biology and medicinal chemistry teams use this type of side-chain-functionalized amino acid derivative to install linkers, attachment points, or scaffold modifications after peptide assembly, enabling controlled preparation of labeled peptides, affinity reagents, or intermediate constructs for SAR studies. The OSu activation supports reliable incorporation of the functionalized residue into peptide frameworks, while the bromomethyl substituent provides a practical electrophilic handle for downstream derivatization without requiring re-synthesis of the amino acid fragment.
3. Bioconjugation Building Block
Boc-His(3-Bom)-OSu is applied as a coupling-ready intermediate for constructing peptide-based bioconjugates where an activated ester format improves reactivity toward amine-containing partners under standard conjugation conditions. Researchers preparing conjugation intermediates often leverage the OSu ester to form amide linkages efficiently, then use the bromomethyl side chain as an additional chemical handle for orthogonal attachment strategies, such as sequential conjugation or attachment to polymers and biomolecular scaffolds. This workflow is particularly relevant for generating multifunctional conjugates that require both a stable amide connection and a secondary reactive site for further assembly into probes, materials, or multicomponent chemical biology tools.
4. Pharmaceutical Intermediate Development
Boc-His(3-Bom)-OSu is also used in the development of protected, side-chain-functionalized intermediates for medicinal chemistry programs that incorporate histidine-containing motifs or histidine-derived linkers into larger structures. Process and R&D chemists value the combination of an activated OSu ester for efficient coupling and a bromomethyl substituent that can be transformed into more specific functional groups during lead optimization. In this context, the derivative functions as a practical intermediate enabling structured diversification: the protected amino acid fragment can be incorporated into a growing sequence or scaffold, and the side-chain electrophile supports later conversion to the desired connectivity pattern for analog synthesis.
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