Substrate engineering and its synthetic utility in the sulfation of primary aliphatic alcohol groups by a bacterial arylsulfotransferase

The use of substrate engineering allowed the enzymatic sulfation by an arylsulfotransferase from Desulfitobacterium hafniense of a number of carbohydrate derivatives. Specific sulfation of carbohydrates chemically or enzymatically is notoriously difficult or complex. As we have shown previously, the arylsulfotransferase is able to sulfate a variety of phenolic alcohols as well as non-phenolic alcohols, albeit the conversion in the latter case is limited and in general less than a few percent. Here we used the strategy of substrate engineering to increase the conversion by attaching a hydrophobic group to the carbohydrate. The formed sulfated intermediates may be used as building blocks in the formation of more complex sulfated carbohydrates via a transglycosylation reaction.