Carbohydrates and their conjugates are recognized by the pharmaceutical industry as an important class of molecules. Antioxidants and their derivatives are attractive natural products due to their interesting anti-cancer, anti-microbial and anti-inflammatory properties. We report here the preparation of carbohydrate-conjugated antioxidants. We have prepared N-glycosylated antioxidants in order to increase their half-life inside the body since the O-glycosides are rather easily hydrolysed by glycosidase. In this work, appropriately protected cinnamic acid derivative antioxidants were coupled with glycosyl azides using a Staudinger chemistry. 1,2-Bis(diphenylphosphino)ethane was used as a catalyst to afford the corresponding N-linked carbohydrate tethered antioxidants. We also report a mild one-pot protocol for the preparation of glycosyl azides directly from free sugars. Our approach for the preparation of glycosyl azides involves the generation of glycosyl bromide intermediates using in situ generated HBr followed by a reaction with sodium azide under mild conditions. The carbohydrate-conjugated antioxidants are expected to possess improved water solubility as well as better bioavailability through internalization via carbohydrate transporters.

N-Linked carbohydrate conjugated antioxidants

251st National Meeting (2016)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.