Glycosidase Catalyzed Synthesis Of Arylalkyl, Phenolic And Ester Glycosides

Hydroxyphenyl propenoic acids and their alcohol derivatives are common components of the human diet and they often occur in plants in the form of various glycosides. As diets rich in polyphenols have been often related to a low incidence of cardiovascular, neurodegenerative, and oncological diseases various food supplements containing these compounds are becoming popular among the general population. In the quest of a convenient biocatalytic entry to these glycosylated nutraceuticals a highly promiscuous fungal rutinosidase (?- rhamnosyl -?-D- from Aspergillus niger and a highly efficient rhamnosidase from A terreus were selected to build a one pot two enzymes, as well as a gram scale scalable, enzymatic entry to arylalkyl glucosides Glucosides were obtained with a productivity up to 7 g L 1 as an example, the a glucoside salidroside, a compound commercialized in Rhodiola rosea nutraceutical formulations was obtained in high isolated yield and purity from tyrosol. Furthermore, during the course of our investigation, we discovered that the rutinosidase from A niger not only efficiently converted hydroxylated aromatic acids eg c oumaric and ferulic acids) into the respective phenolic rutinosides but surprisingly could also catalyze the formation of the respective glycosyl esters representing the first ever reported bioctalyzed synthesis of these compounds.