2-Thiolhistidine is a modified histidine amino acid derivative in which the imidazole-bearing histidine scaffold is functionalized with a thiol group at the 2-position, yielding a sulfur-containing side chain that can participate in redox- and coordination-related chemistry. The molecule contains both an amino group and a carboxyl group for zwitterionic behavior, while the side chain features an imidazole ring alongside the thiol functionality, with stereochemistry not specified in the product name. In biochemical and peptide chemistry workflows, 2-Thiolhistidine is used as a building block or substrate analogue for preparing thiol-functionalized peptides, enabling chemical handle introduction for conjugation, crosslinking, or structure-activity studies that probe histidine/imidazole and thiol side-chain contributions.
CAT No: CP24401
2-Thiolhistidine is a histidine-derived amino acid building block featuring a thiol functional group at the 2-position, enabling direct chemical reactivity beyond the native imidazole side chain. As a sulfur-containing amino acid, it is commonly handled as a reactive intermediate for selective thiol chemistry and for constructing cysteine-like functionalities in peptide and biomolecule contexts. In research workflows, the combination of an imidazole moiety and a free thiol supports coordination and nucleophilic capture strategies used in chemical biology, peptide functionalization, and materials surface chemistry.
1. Peptide Thiol Functionalization
2-Thiolhistidine is used by peptide chemists to introduce a thiol-bearing histidine motif into custom peptides and peptide conjugates, supporting downstream coupling, capture, or controlled crosslinking steps. Researchers often select this building block when they want thiol reactivity while retaining the imidazole functionality for metal coordination or pH-responsive behavior in chemical systems. In practice, it is incorporated into peptide sequences during synthesis workflows to generate defined thiol handles for subsequent conjugation to linkers, polymers, or biomolecule carriers, where site-specific thiol availability is critical for reproducible labeling density and reaction control.
2. Bioconjugation And Linker Chemistry
2-Thiolhistidine is applied in bioconjugation workflows where thiol-directed coupling is required, including preparation of protein or peptide conjugates for chemical biology assays and reagent development. The thiol group provides a reactive handle for forming thioether or disulfide-linked intermediates with electrophilic partners, enabling controlled attachment of functional moieties such as affinity tags, imaging labels, or affinity surfaces. Teams developing conjugate reagents for research use value the presence of both imidazole and thiol functionality because it can improve the chemical design space for coordination-assisted assembly, linker stability studies, and comparative conjugation strategies across different thiol-containing amino acid building blocks.
3. Biomaterials Surface And Crosslinking
2-Thiolhistidine is used in biomaterials research to functionalize surfaces and to create thiol-mediated crosslinking architectures for hydrogels, coatings, and biointerfaces. Materials scientists leverage the thiol functionality to enable covalent immobilization onto thiol-reactive surfaces or to participate in controlled network formation when combined with complementary crosslinking chemistries. The imidazole moiety offers an additional chemical handle for designing coordination-driven interactions or for tuning local microenvironments in polymer and surface formulations, supporting studies of adhesion, immobilization stability, and structure-property relationships in engineered materials.
4. Coordination Chemistry Building Block
2-Thiolhistidine is employed as a sulfur-containing amino acid ligand in coordination chemistry experiments and in the preparation of metal-binding motifs for analytical and materials applications. Researchers use the thiol and imidazole functionalities to design defined binding environments that can be interrogated in solution-phase studies or incorporated into larger constructs such as peptide-based ligands and surface-bound chelators. This building block is particularly useful when a ligand scaffold is needed that combines a soft sulfur donor with an imidazole nitrogen donor, supporting comparative studies of metal capture, exchange behavior, and ligand performance in chemically defined systems.
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