Boc-His(3-Bom)-OMe · HCl

Boc-His(3-Bom)-OMe · HCl is a Boc-protected histidine derivative supplied as an HCl salt, combining an N-terminal Boc protecting group with a side-chain protected imidazole functionality and a methyl ester at the C-terminus. The 3-Bom (benzyloxymethyl) protection on the histidine side chain is designed to control imidazole reactivity during peptide assembly, while the ester form supports downstream coupling and segment condensation workflows. This protected, salt-form amino acid is typically handled in peptide synthesis and intermediate development where orthogonal stability and controlled deprotection are required for clean formation of histidine-containing sequences.

1. Solid-Phase Peptide Synthesis

Boc-His(3-Bom)-OMe · HCl is used by peptide synthesis groups to incorporate histidine residues with minimized side-chain interference, particularly when forming histidine-rich segments. The Boc group provides reliable N-terminal protection under standard peptide coupling/deprotection cycles, while the 3-Bom imidazole protection helps suppress unwanted side reactions from the histidine side chain during chain elongation. The methyl ester format is commonly selected in workflows where protected amino acid building blocks are assembled into peptide fragments and then converted to the appropriate reactive form for subsequent coupling steps.

2. Histidine-Containing Segment Coupling

Boc-His(3-Bom)-OMe · HCl is frequently selected for solution-phase segment condensation and intermediate preparation in custom peptide manufacturing research. The controlled protection pattern supports the assembly of peptide fragments where histidine's imidazole functionality would otherwise complicate activation chemistry or promote side reactions. By using this derivative as a defined, protected unit, researchers can build longer sequences with improved handling consistency, then proceed to the next synthetic stage after converting the ester functionality into the required coupling handle for fragment joining.

3. Pharmaceutical Peptide Intermediate Development

Boc-His(3-Bom)-OMe · HCl is well aligned with the preparation of protected histidine-containing intermediates used in medicinal chemistry programs developing peptide-like candidates and lead optimization libraries. The combination of N-terminal Boc protection, side-chain imidazole protection (3-Bom), and a C-terminal ester provides a stable, well-defined intermediate platform that can be advanced through iterative synthesis steps to reach the desired protected peptide framework. Teams in small-molecule/peptide discovery and process chemistry commonly use this type of building block to manage chemoselectivity during scale-up-oriented intermediate synthesis and to reduce variability across library members.

4. Peptide Library Construction

Boc-His(3-Bom)-OMe · HCl supports peptide library construction where reproducible incorporation of histidine is required across multiple sequence variants. In parallel synthesis workflows, the protected imidazole reduces heterogeneity caused by uncontrolled histidine side-chain behavior, helping maintain consistent coupling outcomes and downstream purification profiles. Researchers building focused libraries for structure-activity relationship studies or receptor-binding investigations often rely on such protected histidine derivatives to standardize the synthetic input while varying other sequence positions.

1. Autoinhibition and phosphorylation-induced activation of phospholipase C-γ isozymes

2. Extended exenatide administration enhances lipid metabolism and exacerbates pancreatic injury in mice on a high fat, high carbohydrate diet

3. Immune responses to peptides containing homocitrulline or citrulline in the DR4-transgenic mouse model of rheumatoid arthritis

4. Spatiotemporal delivery of nanoformulated liraglutide for cardiac regeneration after myocardial infarction

5. Olfactory receptor based piezoelectric biosensors for detection of alcohols related to food safety applications