Mantyl tagged oligo alpha (1 -> 2) mannosides as Candida albicans beta-mannosyl transferases substrates: a comparison between synthetic strategies
2013
Pourcelot, Marilyne | Cattiaux, Laurent | Sfihi-Loualia, Ghenima | Fabre, Emeline | Krzewinski, Frédéric | Fradin, Chantal | Poulain, Daniel | Delplace, Florence | Guerardel, Yann | Mallet, Jean-Maurice
Fluorescent oligomannosides are important tools for the evaluation of mannosyl transferase activities and selectivities. In a project dealing with Candida albicans beta-mannosyl transferases, three mantyl tagged alpha (1 -> 2) oligomannosides were prepared by different ways: using all ester strategy compatible with the presence of an azido group suitable for direct click chemistry; and alternatively using the more classic benzyl protecting groups. Although more elegant, the all ester strategy has shown important limitations: reduced reactivity of mannosyl donors, and 3 -> 2 ester migration. Preliminary enzymatic studies have shown that the synthetic oligomannosides are efficient substrate of b-mannosyl transferases.
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