| DOI | Resolve DOI: https://doi.org/10.1039/c2sc01077a |
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| Author | Search for: Forget, Stephanie M.; Search for: Bhattasali, Debabrata; Search for: Hart, V. Catherine; Search for: Cameron, T. Stanley; Search for: Syvitski, Ray T.1; Search for: Jakeman, David L. |
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| Affiliation | - National Research Council of Canada. NRC Institute for Marine Biosciences
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| Format | Text, Article |
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| Abstract | Ketose-phosphonates may adopt open chain, or α- or β-furanosyl, or α- or β-pyranosyl configurational isomers in aqueous solution. An HPLC and NMR analysis of a series of ketose-phosphonates with a thymidylyltransferase (dTDP-glucose pyrophosphorylase) implied a rapid dynamic equilibrium between the pyranosyl forms of gluco-ketose phosphonate leading to efficient production of unique sugar nucleotide analogues. The preparation of diastereomerically pure gluco-configured monofluoromethylenephosphonates enabled the determination of the thymidylyltransferase preference for CHF stereochemistry. The effects of acidity upon thymidylyltransferase substrate specificity were determined using a series of monofluoro- and difluoro- ketose-phosphonates. WaterLOGSY NMR spectroscopy demonstrated a switching of the ordered Bi-Bi mechanism with ketose-phosphonate substrates. Ketose-phosphonates are presented as a unique class of sugar 1-phosphate analogues with potential applications as glycosyltransferase probes. |
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| Publication date | 2012-03-16 |
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| In | |
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| Language | English |
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| Peer reviewed | Yes |
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| NPARC number | 21268964 |
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| Export citation | Export as RIS |
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| Report a correction | Report a correction (opens in a new tab) |
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| Record identifier | a5eed3d8-3eef-4700-8252-af257917ae3b |
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| Record created | 2013-11-28 |
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| Record modified | 2020-04-21 |
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