Oligosaccharides are increasingly useful in the fields of food, pharmaceuticals, and biochemical research. For food manufacturers, oligosaccharides are not only valuable as sweeteners, but as prebiotics they are important for cultivating healthy gut flora, and the natural occurrence of oligosaccharides in breastmilk has sparked interest among infant formula manufacturers. On the basic science side, oligosaccharides play an important role at the level of cell surface interactions and contribute to diseases from cancer to muscular dystrophy. Regardless of the application, though, carbohydrate production is a non-trivial process. We present a fast and simple yet robust method for constructing oligosaccharides, which could form the basis for automated carbohydrate synthesis.
Description
This novel one-pot glycosylation system uses a designer thioglycoside and global deprotection to streamline the oligosaccharide assembly process. Traditionally, carbohydrate chain elongation involves oxophilic or thiophilic activators, which are incompatible with acid-sensitive protecting groups. Instead, our system uses a carbophilic activator, which both facilitates glycosidic linkage formation and supports protecting groups that a common acid can remove all at once from the completed carbohydrate. Not only is this system faster and more user-friendly than existing methods, but with a yield greater than 93 percent for most oligosaccharides, it’s also more efficient.
Applications
Prebiotics
Infant formula
Fat or sugar substitute
Food texture improvement
Glycobiology research
Drug discovery
Advantages
Faster oligosaccharide synthesis
Excellent yield at room temperature
Easy to prepare and use
Shelf-stable and tolerant to protecting group manipulation
Invention Readiness
Tested in the laboratory
IP Status
https://patents.google.com/patent/US9399655B2
