Substrate Engineering and its Synthetic Utility in the Sulfation of Primary Aliphatic Alcohol Groups by a Bacterial Arylsulfotransferase. Issue 12 (13th August 2015)

• Record Type: Journal Article
• Authors: Hartog, Aloysius F.; Wever, Ron
• Is Part Of: Advanced synthesis & catalysis. Volume 357:Issue 12(2015)
• Page Start: 2629
• Page End: 2632
• Publication Date: 2015-08-13
• Subjects: Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201500482
• Languages: English
• ISSNs: 1615-4150

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>The use of substrate engineering allowed the enzymatic sulfation by an arylsulfotransferase from <italic>Desulfitobacterium hafniense</italic> 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 <italic>via</italic> a transglycosylation reaction.</p> <p> <graphic position="anchor" mimetype="image" xlink:href="ark:/27927/pgj2fzmk63v" orientation="portrait" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink" /> </p> </abstract>