122888-91-9Relevant academic research and scientific papers
Exploiting Acid Phosphatases in the Synthesis of Phosphorylated Monoalcohols and Diols
Tasndi, Gbor,Lukesch, Michael,Zechner, Michaela,Jud, Wolfgang,Hall, Mlanie,Ditrich, Klaus,Baldenius, Kai,Hartog, Aloysius F.,Wever, Ron,Faber, Kurt
, p. 45 - 50 (2016)
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.
ENZYMATIC SYNTHESIS OF PHOSPHORIC MONOESTERS WITH ALKALINE PHOSPHATASE IN REVERSE HYDROLYSIS CONDITIONS
Pradines, A.,Klaebe, A.,Perie, J.,Paul, F.,Monsan, P.
, p. 6373 - 6386 (2007/10/02)
Title compounds were synthesized on a preparative scale using alkaline phosphatase, orthophosphoric monoester phosphohydrolase E.C. 3.1.3.1., in reverse hydrolysis conditions.Optimization for one of the 25 phosphoryl acceptors investigated (glycerol) shows that up to 55percent synthesis yield can be obtained using a large excess of substrate, conditions in which the enzymatic activity remains high.From the results obtained with different phosphoryl group donors, phosphate, pyrophosphate and polyphosphates and with enzymes of different sources, it comes up that the best results are obtained with pyrophosphate and with the weakly purified calf intestine alkaline phosphatase.The extent of enzymatic hydrolysis of the donor can be reduced owing to the existence of two different pH optima for the two reactions, phosphorylation and hydrolysis.The synthesis can be also performed using inert co-solvents which allow to reduce the amount of acceptor used, as long as Zn++ is added to the reaction medium.The results are discussed in terms of the catalytic mechanism of alkaline phosphatase.
