Metabolism of 2-deoxy-2-fluoro-D-[3H]glucose and 2-deoxy-2-fluoro-D-[3H]mannose in yeast and chick-embryo cells.
2-Deoxy-2-fluoro-D-[3H]glucose and 2-deoxy-2-fluoro-D-[3H]mannose have been prepared by tritiation of the corresponding unlabeled 2-fluoro sugars. The tritiated 2-fluoro sugars are phosphorylated and activated by UTP and by GTP to yield UDP-2-deoxy-2-fluoro-D-[3H]glucose, UDP-2-deoxy-2-fluoro-D-[3H]mannose, GDP-2-deoxy-2-fluoro-D-[3H]glucose and GDP-2-deoxy-2-fluoro-D-[3H]mannose in both cell types. The nucleotide derivatives could also be labeled in the nucleotide moiety by feeding the cells with [14C]uridine or [14C]guanosine in the presence of unlabeled 2-fluoro sugar. No evidence was obtained for metabolic steps in which the six-carbon chain of 2-fluoro sugars was not preserved. No epimerisation of the label to 2-deoxy-2-fluoro-D-[3H]galactose could be observed by radioactive gas-liquid chromatography of the enzymatic cleavage products of the different 2-fluoro sugar metabolites isolated from either cell type. Yeast and chick embryo cells both incorporate 2-deoxy-2-fluoro-D-[3H]glucose and 2-deoxy-2-fluoro-D-[3H]mannose specifically into glycoproteins, although this incorporation is very low when compared to the incorporation of 2-deoxy-D-[3H]glucose.
D000818:Animals; D002473:Cell Wall / Q000378:metabolism; D002478:Cells, Cultured; D002642:Chick Embryo; D003837:Deoxy Sugars / Q000378:metabolism*; D003847:Deoxyglucose / Q000031:analogs & derivatives / Q000378:metabolism*; D006023:Glycoproteins / Q000096:biosynthesis; D006156:Guanosine Diphosphate Sugars / Q000378:metabolism; D007536:Isomerism; D011134:Polysaccharides / Q000096:biosynthesis; D012210:Rhamnose / Q000031:analogs & derivatives* / Q000378:metabolism; D012441:Saccharomyces cerevisiae / Q000378:metabolism; D014539:Uridine Diphosphate Sugars / Q000378:metabolism
D003837:Deoxy Sugars; D006023:Glycoproteins; D006156:Guanosine Diphosphate Sugars; D011134:Polysaccharides; D014539:Uridine Diphosphate Sugars; D003847:Deoxyglucose; D012210:Rhamnose