NDLI: Synthesis and enzymatic evaluation of ketose phosphonates: the interplay between mutarotation, monofluorination and acidity

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Chemical Science Vol - 3 Issue - 5

Chemical Science Vol - 3 Issue - 4

Chemical Science Vol - 3 Issue - 3

Chemical Science Vol - 3 Issue - 2

Chemical Science Vol -2

Chemical Science Vol -1

Synthesis and enzymatic evaluation of ketose phosphonates: the interplay between mutarotation, monofluorination and acidity

Content Provider	Royal Society of Chemistry (RSC)
Author	Forget, Stephanie M. Syvitski, Ray T. Jakeman, David L. Hart, V. Catherine Cameron, T. Stanley Bhattasali, Debabrata
Copyright Year	2012
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.
Starting Page	1866
Ending Page	1878
Page Count	13
File Format	HTM / HTML PDF
ISSN	20416520
Volume Number	3
Issue Number	6
Journal	Chemical Science
DOI	10.1039/c2sc01077a
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Swiss franc Sucrose Glycosyltransferase Phosphate Thymidine diphosphate glucose Nucleotide Nuclear magnetic resonance spectroscopy Stereochemistry Cis\u2013trans isomerism High-performance liquid chromatography Phosphonate Dynamic equilibrium
Content Type	Text
Resource Type	Article
Subject	Chemistry

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