On the preparation of carbohydrate-protein conjugates using the traceless Staudinger ligation

C Grandjean, A Boutonnier, C Guerreiro…

Index: Grandjean, Cyrille; Boutonnier, Alain; Guerreiro, Catherine; Fournier, Jean-Michel; Mulard, Laurence A. Journal of Organic Chemistry, 2005 , vol. 70, # 18 p. 7123 - 7132

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Citation Number: 117

Abstract

The nature of a linker used for preparing glycoconjugate vaccines is of utmost importance as it may lead to immunogenic biomolecules. We report the conjugation of carbohydrate haptens to protein carriers leading to potential vaccines using the traceless Staudinger ligation. The ligation relies on the selective transfer of a phosphane substituent to an azide to form a native amide bond in the final product upon release of an oxidized phosphane ...