Multivalency effects in carbohydrate binding play a key role in many biological processes. Recently defined poly/oligo(amidoamines) (PAAs) have been recognized for their potential as well-defined scaffolds for multivalent carbohydrate presentation. Here we present three complimentary strategies for the preparation of sequence-defined carbohydrate-functionalised PAAs by photochemical thiol�ene coupling (TEC). PAAs presenting multiple olefins were obtained by solid-phase synthesis with novel tailor-made diethylenetriamine based building blocks and subsequently conjugated with unprotected thio-carbohydrates. Alternatively, pre-functionalised glyco-building blocks were prepared by TEC and subsequently coupled on solid support to provide carbohydrate-functionalised PAAs. Both methods rely on the use of a continuous flow photoreactor for carbohydrate conjugation. Furthermore a highly efficient thiol-ene protocol for carbohydrate conjugation onto multicomponent complex scaffolds was developed.These novel glyco-oligo(amidoamines) are used to answer fundamental questions concerning the multivalent binding effect of carbohydrates as well as in the field of vaccination and cell-specific DNA/RNA targeting.

Precise, sequence-defined glyco-oligo(amidoamines) for multivalent carbohydrate interactions via thiol-ene chemistry

245th National Meeting (2013)

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