Enzymatic Synthesis of Nucleoside-5′-O-(1-thiophosphates) and (SP)-Adenosine-5′-O-(1-thiotriphosphate)
| Autor: | A. I. Zinchenko, Olga I. Titovich, Elena N. Kalinichenko, Elena B. Rubinova, Sergei V. Kvach, Vladimir N. Barai, Igor A. Mikhailopulo |
|---|---|
| Rok vydání: | 2003 |
| Předmět: |
chemistry.chemical_classification
Stereochemistry Organic Chemistry General Medicine Phosphate Biochemistry Adenosine Catalysis Thiophosphate Trimethyl phosphate Inorganic Chemistry chemistry.chemical_compound Enzyme Column chromatography chemistry Drug Discovery Nucleoside phosphotransferase medicine Physical and Theoretical Chemistry Nucleoside medicine.drug |
| Zdroj: | Helvetica Chimica Acta. 86:2827-2832 |
| ISSN: | 1522-2675 0018-019X |
| DOI: | 10.1002/hlca.200390233 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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