Examples of Glycomimetics with Sulfur in the Ring

Only a small number of sugars and related compounds with sulfur in the ring have been reported as natural products. In the following, some select and stmcturally quite dissimilar examples will be discussed. 

A wide variety of synthetic sugar and nucleoside mimicking compounds with sulfur in the ring have been prepared for basic research, with a view to producing biologically active compounds with improved biochemical properties. Various classes of compounds are discussed in the following paragraphs. 

FIGURE 9.10 5-Thio-D-xylose (11), l,5-anhydro-5-thio-D-mannitol (41). 

Maltoside analogs with 5-thioglucose at the nonreducing end and the corresponding k-thioglycosides were prepared as potential glycosidase inhibitors by the same group [79,80]. 

No pronounced biological effects were reported for 6-thio-D-fructopyranose 36. Nonetheless, this compound was found to be unusually sweet and essentially nontoxic to mice [86]. In addition to its chemical synthesis [87], an enzymatic preparation from 6-thio-D-glucose employing glucose isomerase (EC 5.3.1.5) was reported [88]. In keeping with the general properties of pyranoid ring 

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Examples of Glycomimetics with Sulfur in the Sugar Ring. 2008... 

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