STICS: surface-tethered iterative carbohydrate synthesis

摘要

A new surface-tethered iterative carbohydrate synthesis (STICS) technology is presented in which a surface functionalized 'stick' made of chemically stable high surface area porous gold allows one to perform cost efficient and simple synthesis of oligosaccharide chains; at the end of the synthesis, the oligosaccharide can be cleaved off and the stick reused for subsequent syntheses.rnCarbohydrates are the most abundant molecules on Earth, yet our ability to chemically synthesize these complex natural compounds to keep pace with rapidly evolving areas of glycomics is still far from being satisfactory. In spite of significant progress in the area of synthetic carbohydrate chemistry, there is a constant need for improved methods. Recent years have witnessed a new loop of discovery of high throughput technologies for expeditious oligosaccharide assembly; their syntheses in a one-pot fashion, by using an automated synthesizer, or in a microreactor are only a few of the recent notable breakthroughs.rnHerein we describe a new complementary technology that we call STICS (surface-tethered iterative carbohydrate synthesis). This technique is aimed at overcoming some of the limitations associated with traditional solid-phase synthesis of oligosaccharides, such as limited use of molecular sieves, large volume of waste solvent, resin poisoning, reagent trapping, and difficulties in the construction of compound libraries. As illustrated in Scheme 1, at the basis of the STICS concept is a surface functionalized 'stick' made of chemically stable high surface area material that would simplify the transformation of the solid support-bound molecules between the reaction vessels. The glycosyl acceptor-anchored stick (A) is placed in the reaction vessel (B), containing sufficient quantities of the glycosyl donor, promoter and molecular sieves.