| DOI | Trouver le DOI : https://doi.org/10.1039/c2sc01077a |
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| Auteur | Rechercher : Forget, Stephanie M.; Rechercher : Bhattasali, Debabrata; Rechercher : Hart, V. Catherine; Rechercher : Cameron, T. Stanley; Rechercher : Syvitski, Ray T.1; Rechercher : Jakeman, David L. |
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| Affiliation | - Conseil national de recherches du Canada. Institut des biosciences marines du CNRC
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| Format | Texte, Article |
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| Résumé | 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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| Date de publication | 2012-03-16 |
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| Dans | |
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| Langue | anglais |
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| Publications évaluées par des pairs | Oui |
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| Numéro NPARC | 21268964 |
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| Exporter la notice | Exporter en format RIS |
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| Signaler une correction | Signaler une correction (s'ouvre dans un nouvel onglet) |
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| Identificateur de l’enregistrement | a5eed3d8-3eef-4700-8252-af257917ae3b |
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| Enregistrement créé | 2013-11-28 |
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| Enregistrement modifié | 2020-04-21 |
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