Synthetic routes targeting agrocinopines, bacterial carbohydrate phosphodiesters, and their analogues
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Published:15 Dec 2021
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Special Collection: 2021 ebook collection
Q. Zhang, S. Li, M. Ahmar, L. Soulère, and Y. Queneau, in Carbohydrate Chemistry: Chemical and Biological Approaches, Volume 45, ed. A. Pilar Rauter, T. K. Lindhorst, and Y. Queneau, The Royal Society of Chemistry, 2021, vol. 45, pp. 109-130.
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Agrocinopines are carbohydrate phosphodiesters produced by pathogenic bacteria of the genus of Agrobacterium. Their role in the infection process of plants by Agrobacterium strains has been highlighted resulting from considerable work from microbiologists. On the synthetic chemistry side, several approaches towards agrocinopines or their analogs have been reported, either as a contribution to their structural characterization or as partial or total synthesis challenges. Studies have also been directed towards the design of specific analogs. This chemical side of bacterial phosphodiesters of the agrocinopine family is overviewed below, highlighting the key challenges, which are the choice of appropriate partially protected building blocks and the methods for connecting them through a phosphoryl linkage.