Chitotriose consists of three β(1→4)-linked N-acetyl-D-glucosamine (GlcNAc) units, forming the trisaccharide GlcNAc-β(1→4)-GlcNAc-β(1→4)-GlcNAc with the molecular formula C18H35N3O13 and a molecular weight of 501.5 g/mol. The N-acetylated variant, N,N',N''-triacetylchitotriose (C24H41N3O16, 627.6 g/mol), features acetamido groups at the 2-position of each GlcNAc and is commonly used in enzymatic assays. This linear structure derives from chitin hydrolysis, with the reducing end existing as either an open-chain aldose or a cyclic pyranose.
Sources and Preparation
Chitotriose occurs as a degradation product of chitin, the β(1→4)-linked GlcNAc polymer present in fungal cell walls and arthropod exoskeletons. It is often prepared through endo-chitinase hydrolysis. The triacetylated form, triacetyl-chitotriose, serves as a substrate for endo-chitinases and enables precise enzymatic activity measurement, typically available at >95% purity.
Biological Roles and Applications
Chitotriose exhibits antibacterial activity against pathogens such as Salmonella, a property attributed to its chitooligosaccharide-mediated disruption of microbial membranes. It is used in the preparation of biotinylated glycans and serves as a structural model for studying chitin recognition mechanisms in plant and animal immunity. Analytical applications include HPLC purification and conformational studies of flexible glycan structures.
