Enzyme-Catalyzed Synthesis of Furanosyl Nucleotides
A bacterial α-d-glucopyranosyl-1-phosphate thymidylyltransferase was found to couple four hexofuranosyl-1-phosphates, as well as a pentofuranosyl-1-phosphate, with deoxythymidine 5‘-triphosphate, providing access to furanosyl nucleotides. The enzymatic reaction mixtures were analyzed by electrospray...
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| Veröffentlicht in: | Organic letters 2008-01, Vol.10 (2), p.161-163 |
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| container_title | Organic letters |
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| creator | Timmons, Shannon C Hui, Joseph P. M Pearson, Jessica L Peltier, Pauline Daniellou, Richard Nugier-Chauvin, Caroline Soo, Evelyn C Syvitski, Ray T Ferrières, Vincent Jakeman, David L |
| description | A bacterial α-d-glucopyranosyl-1-phosphate thymidylyltransferase was found to couple four hexofuranosyl-1-phosphates, as well as a pentofuranosyl-1-phosphate, with deoxythymidine 5‘-triphosphate, providing access to furanosyl nucleotides. The enzymatic reaction mixtures were analyzed by electrospray ionization mass spectrometry and NMR spectroscopy to determine the anomeric stereochemistry of furanosyl nucleotide products. This is the first demonstration of a nucleotidylyltransferase discriminating between diastereomeric mixtures of sugar-1-phosphates to produce stereopure, biologically relevant furanosyl nucleotides. |
| doi_str_mv | 10.1021/ol7023949 |
| format | Article |
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| identifier | ISSN: 1523-7060 |
| ispartof | Organic letters, 2008-01, Vol.10 (2), p.161-163 |
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| language | eng |
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| source | MEDLINE; American Chemical Society Journals |
| subjects | Catalysis Molecular Structure Nucleotides - chemical synthesis Nucleotides - chemistry Nucleotidyltransferases - metabolism Stereoisomerism Substrate Specificity |
| title | Enzyme-Catalyzed Synthesis of Furanosyl Nucleotides |
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