The glycosylation of steroids

A Glycosynthase Catalyst for the Synthesis of Flavonoid Glycosides

“…[5] Novel synthetic routes to such compounds provide a powerful tool for exploring not only this activity by providing ready access to probes, standards, and inhibitors but also to the many plant natural products such as flavonoids and steroid glycosides that have been implicated as potential therapeutics. [6][7][8][9][10][11][12] Despite the many elegant methods for chemical glycosylation, [13] methods for direct regioselective glycosylation of acceptors are limited, [14] which has led to a heavy dependence upon protecting-group regimes that introduce many additional steps. The often exquisite selectivity of biocatalytic methods provides the potential to overcome such problems.…”

Enzymatic Synthesis of Anabolic Steroid Glycosides by Glucosyltransferase from Terribacillus sp. PAMC 23288

“…Lipophilic steroids, such as steroid ester derivatives, have been studied in detail; in contrast, studies on hydrophilic steroids are scant. Hydrophilic steroids can be prepared by glycosylation [ 28 ], but the yield of conventionally prepared glycosylated products is insufficient and the process is complicated [ 29 , 30 ]. In addition, investigations into steroid glycosylation might have been avoided because testosterone glycosides have considerably lower local bioactivity than the ester forms [ 31 - 33 ].…”

Facile synthesis of tetrasaccharide fragments of bioactive Asterosaponins novaeguinosides I and II from starfish Culcita novaeguineae

“…So, poor accessibility of these molecules has retarded in-depth studies on their biosynthetic pathway biological activities. 15,16 Also the structures of carbohydrate moieties in starfish asterosaponin are often very complex and so far there is only a few synthetic work reported on this field. [17][18][19][20] The efficient synthesis of the oligosaccharide chain is not a trivial task.…”