At NINGBO INNO PHARMCHEM CO.,LTD., we provide the chemical building blocks that form the foundation of scientific discovery. For those specializing in peptide chemistry, understanding the specific properties and applications of protected amino acids is crucial. This article offers an in-depth look at Boc-His(Tos)-OH, exploring its chemical structure, the rationale behind its protection strategy, and its indispensable role in modern peptide synthesis.

Histidine is one of the 20 standard amino acids, characterized by its unique imidazole side chain. This side chain is amphoteric, capable of acting as both a proton donor and acceptor, making histidine a critical residue in the active sites of many enzymes and in protein-ligand interactions. However, this reactivity also necessitates careful management during peptide synthesis. The Boc SPPS strategy utilizes protecting groups to control reactivity. For histidine, N-alpha-Boc-N-im-tosyl-L-histidine, or Boc-His(Tos)-OH, is a standard choice. The tert-butyloxycarbonyl (Boc) group on the alpha-amino terminus prevents its participation in unwanted amide bond formation prematurely. Simultaneously, the p-toluenesulfonyl (tosyl) group attached to the imidazole ring effectively masks its nucleophilicity and potential for side reactions, such as alkylation or acylation, during the peptide assembly process.

The choice of the tosyl group for imidazole protection in Boc-His(Tos)-OH is strategic. It offers a balance of stability during the Boc SPPS cycle and ease of removal under specific acidic conditions, typically with TFA. This controlled deprotection ensures that the histidine side chain is only revealed when intended, typically at the final cleavage step or during specific orthogonal deprotection strategies if employed. The molecular formula C18H23N3O6S and molecular weight of approximately 409.46 g/mol are key identifiers for this compound. Researchers looking to buy Boc-His(Tos)-OH can trust NINGBO INNO PHARMCHEM CO.,LTD. for a product that adheres to these chemical specifications, ensuring predictable synthesis outcomes.

The applications of Boc-His(Tos)-OH extend across various research domains, including the synthesis of biologically active peptides for pharmaceutical research, the development of enzyme substrates, and the creation of peptide-based materials. Its reliable performance in custom peptide synthesis makes it a staple in laboratories dedicated to advancing peptide science. The ability to accurately incorporate histidine residues with protected side chains significantly streamlines complex synthesis pathways, contributing to greater efficiency and higher purity of the final peptide products.

In essence, Boc-His(Tos)-OH is a testament to the sophisticated chemistry employed in peptide synthesis. Its carefully designed protective groups make it an essential tool for researchers needing to precisely integrate histidine into their peptide constructs. NINGBO INNO PHARMCHEM CO.,LTD. is proud to supply this high-quality reagent, supporting the critical work of scientists worldwide.