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Exploiting Acid Phosphatases in the Synthesis of Phosphorylated Monoalcohols and Diols
Author(s) -
Tasnádi Gábor,
Lukesch Michael,
Zechner Michaela,
Jud Wolfgang,
Hall Mélanie,
Ditrich Klaus,
Baldenius Kai,
Hartog Aloysius F.,
Wever Ron,
Faber Kurt
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201501306
Subject(s) - chemistry , phosphate , polyphosphate , phosphatase , phosphorylation , hydrolysis , stereoselectivity , enzyme , organic chemistry , catalysis , combinatorial chemistry , biochemistry
Abstract 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.