Exploiting Acid Phosphatases in the Synthesis of Phosphorylated Monoalcohols and Diols.

Tasnádi, Gábor; Lukesch, Michael; Zechner, Michaela; Jud, Wolfgang; Hall, Mélanie; Ditrich, Klaus; Baldenius, Kai; Hartog, Aloysius F.; Wever, Ron; Faber, Kurt

A set of phosphatases was evaluated for their potential to catalyze the regio- and stereoselective phosphorylation of alcohols using a high-energy inorganic phosphate donor, such as di-, tri- and polyphosphate. Parameters such as type and amount of phosphate donor and pH of the reaction were investigated in order to minimize the thermodynamically favored hydrolysis of the phosphate donor and the formed phosphate ester. Diols were monophosphorylated with high selectivities. This biocatalytic phosphorylation method provides selectively activated and/or protected synthetic intermediates for further chemical and/or enzymatic transformations and is applicable to a large scale (6.86 g) in a flow setup with immobilized phosphatase.

PHOSPHATASES; STEREOSELECTIVE reactions; PHOSPHORYLATION; PHOSPHATES; BIOCATALYSIS

European Journal of Organic Chemistry, 2016, Vol 2016, Issue 1, p45

1434-193X

Academic Journal

10.1002/ejoc.201501306