Di-tert-butyl diethylphosphoramidite as the phosphitylating reagent in the preparation of 3-deoxy-3-C-methylene-D-ribo-hexose-6-phosphate and 3-deoxy-3-C-methylene-D-erythro-pentose-5-phosphate.
3-Deoxy-3-C-methylene-D-ribo-hexose-6-phosphate and 3-deoxy-3-C-methylene-D-erythro-pentose-5-phosphate were prepared from a common intermediate 3-deoxy-3-C-methylene-1,2-O-isopropylidene-alpha-D-ribo-hexofuranose. The preparation of the phosphorylated unsaturated sugars employed di-tert-butyl diethylphosphoramidite as the phosphitylating reagent. The removal of all the protecting groups was done under acidic conditions in the ultimate step. The unsaturated sugar phosphates were competitive inhibitors but neither substrates nor inactivators of glucose-6-phosphate and ribose-5-phosphate isomerases.
Burger
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A
Laboratoire de Chimie Organique Biologique associé au CNRS UMR 7509, Faculté de Chimie, Université Louis Pasteur, Strasbourg, France. aburger@chimie.u-strasbg.fr
Tritsch
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D
Biellmann
J F
JF
D019747:Aldose-Ketose Isomerases / Q000037:antagonists & inhibitors / Q000378:metabolism*; D001667:Binding, Competitive; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000494:pharmacology; D006863:Hydrogen-Ion Concentration; D009943:Organophosphorus Compounds / Q000494:pharmacology; D013329:Structure-Activity Relationship; D013379:Substrate Specificity; D013403:Sugar Phosphates / Q000138:chemical synthesis* / Q000378:metabolism / Q000494:pharmacology
C440771:3-deoxy-3-C-methylene-erythro-pentose-5-phosphate; C440770:3-deoxy-3-C-methylene-ribo-hexose-6-phosphate; D004791:Enzyme Inhibitors; D009943:Organophosphorus Compounds; D013403:Sugar Phosphates; C440768:di-tert-butyl diethylphosphoramidite; D019747:Aldose-Ketose Isomerases; C023298:xylose isomerase; C022548:ribosephosphate isomerase