Synthesis of carbohydrate-scaffolded thymine glycoconjugates to organize multivalency

Abstract

Multivalency effects are essential in carbohydrate recognition processes as occurring on the cell surface. Thus many synthetic multivalent glycoconjugates have been developed as important tools for glycobiological research. We are expanding this collection of molecules by the introduction of carbohydrate-scaffolded divalent glycothymine derivatives that can be intramolecularily dimerized by [2 + 2] photocycloaddition. Thus, thymine functions as a control element that allows to restrict the conformational flexibility of the scaffolded sugar ligands and thus to “organize” multivalency. With this work we add a parameter to multivalency studies additional to valency.

Keywords

• [2 + 2] photocycloaddition
• carbohydrate scaffolds
• multivalency
• thymine glycoconjugates