Recent advances in photoinduced glycosylation: Oligosaccharides, glycoconjugates and their synthetic applications

Abstract

Carbohydrates have been demonstrated to perform crucial tasks in biological processes. However, the advancement in carbohydrate research is relatively slow due to the problems associated with the complexity of carbohydrate structures and the lack of general synthetic methods. Considering that the unique process of photoinduced glycosylation is rapidly emerging as a promising tool in carbohydrate chemistry, this academic review inspects the recent evolution in the chemistry of carbohydrates, including mostly synthetic, and to a lesser extent mechanistic aspects, by examining the strategies that apply photoinduced glycosylation in the synthesis of oligosaccharides and glycoconjugates. We have chosen to present several representative examples that illustrate the diverse and advance uses of photoinduced glycosylation in carbohydrate chemistry for the synthesis of oligosaccharides, thiosugars, glycoconjugates and glycoproteins. As simple techniques for obtaining carbohydrate targets, these methods are mild and effective for the construction of glycosidic bonds via photoinduced promoted glycosylation, which is environmentally friendly. We mainly highlight the symbiotic cooperation of photoinduced glycosylation via electron transfer, hydrogen atom transfer and energy transfer with or without photocatalyst for diverse arrays in the field of total synthesis of carbohydrate based vaccines, thiyl radical mediated clustering, chemical biology and material chemistry.