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Enzymatic Synthesis of Nucleoside‐5′‐O‐(1‐thiophosphates) and (SP)‐Adenosine‐5′‐O‐(1‐thiotriphosphate)
Authors:Vladimir&#x;N Barai  Anatoli&#x;I Zinchenko  Sergei&#x;V Kvach  Olga&#x;I Titovich  Elena&#x;B Rubinova  Elena&#x;N Kalinichenko  Igor&#x;A Mikhailopulo
Institution:Vladimir?N. Barai,Anatoli?I. Zinchenko,Sergei?V. Kvach,Olga?I. Titovich,Elena?B. Rubinova,Elena?N. Kalinichenko,Igor?A. Mikhailopulo
Abstract:Treatment of adenosine with PSCl3 in trimethyl phosphate gave, after ion‐exchange chromatography, adenosine‐5′‐O‐monophosphate (AMP; 28%) and adenosine‐5′‐O‐monothiophosphate (AMPS; 48%). AMPS was studied as a thiophosphate residue donor in an enzymatic transphosphorylation with nucleoside phosphotransferase (NPase) of the whole cells of Erwinia herbicola. As exemplified by a number of natural and sugar‐ and base‐modified nucleosides, it was demonstrated that NPase of the whole cells of Erwinia herbicola catalyzes the transfer of both thiophosphate and phosphate residues with a similar efficiency. An incubation of AMPS in a phosphorylating extract of Saccharomyces cerevisiae (K‐phosphate buffer (0.3 M , pH 7.0); 3% glucose; 15 mM MgCl2; 28°, 8 h), followed by ion‐exchange column chromatography afforded AMP (8%), AMPS (recovered, 23%), ATP (11%), and (SP)‐adenosine‐5′‐O‐(1‐thiotriphosphate) ((SP)‐ATPαS); (total yield 37%; 48% based on the consumed AMPS). For comparison of physicochemical properties, adenosine was chemically transformed into ATPαS as a mixture of the (SP) (53%) and (RP) (44%) diastereoisomers.
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