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
Hartog, Aloysius F.,Wever, Ron
supporting information
p. 2629 - 2632
(2015/09/01)
N-acetyl-6-sulfo-D-glucosamine as a promising mimic of N-acetyl neuraminic acid
6-Sulfo-D-GlcNAc with a molecular geometry close to that of N-acetylneuraminic acid (Neu5Ac) was hypothesized to serve as a simple Neu5Ac mimic possessing high potential in biochemical and medicinal applications. The hypothesis was evidenced with a neuraminidase inhibition assay using p-nitrophenyl (pNP) 3-, 4-, and 6-sulfo-β-D-GlcNAc (4, 5 and 2a) and 6-sulfo-β-D-Glc 6, in which only pNP 6-sulfo-β-D-GlcNAc 2a was found to show substantial activity.