Substrate Engineering and its Synthetic Utility in the Sulfation of Primary Aliphatic Alcohol Groups by a Bacterial Arylsulfotransferase

Abstract

Abstract 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. magnified image

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Identifiers

DOI

10.1002/adsc.201500482

Journal

Advanced Synthesis & Catalysis

Year

2015