Exploiting Acid Phosphatases in the Synthesis of Phosphorylated Monoalcohols and Diols. Issue 1 (15th December 2015)

• Record Type: Journal Article
• Authors: Tasnádi, Gábor; Lukesch, Michael; Zechner, Michaela; Jud, Wolfgang; Hall, Mélanie; Ditrich, Klaus; Baldenius, Kai; Hartog, Aloysius F.; Wever, Ron; Faber, Kurt
• Is Part Of: European journal of organic chemistry. Issue 1(2016)
• Page Start: 45
• Page End: 50
• Publication Date: 2015-12-15
• Subjects: Phosphorylation -- Phosphatase -- Biocatalysis -- Regioselectivity -- Inorganic phosphate donors; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201501306
• Languages: English
• ISSNs: 1434-193X

Abstract

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. Abstract : Acid phosphatases were employed to phosphorylate monoalcohols and diols, the latter with high regioselectivity, in the presence of high‐energy inorganic phosphate donors. Kinetically controlled product formation was enabled by proper selection of pH and phosphate donor as well as by a flow setup yielding several grams of phosphorylated product.