Uridine diphosphate 2-deoxyglucose. Chemical synthesis, enzymic oxidation and epimerization.
The paper describes chemical synthesis of uridine diphosphate 2-deocyglucose (UDPdGLc) through reaction of uridine 5'-phosphomorpholidate with 2-deoxy-a-D-glucopyranosyl phosphate. The prepared analog of uridine diphosphate glucose (UDPGlc) served as a substrate for calf liver UDPGlc dehydrogenases (EC 1.1.1.22), the reaction product was identified as nucleotide deoxyhexuronic acid derivative. The apparent Km for UDPdGlc was found to be 60 times that of UDPGlc, and the relative V value for the analog was 0.09. The peculiar lag-eriod in reaction kinetics has been observed for the analog and is presumably connected with the slow rate of the initial stages of the reaction. UDPdGlc was found to be quite an efficient substrate for UDPGlc 4-epimerases (EC 5.13.2) from yeast, calf liver and mung bean seedlings.
D000429:Alcohol Oxidoreductases / Q000378:metabolism; D000818:Animals; D002238:Carbohydrate Epimerases / Q000378:metabolism; D002417:Cattle; D003837:Deoxy Sugars; D003847:Deoxyglucose / Q000031:analogs & derivatives; D007700:Kinetics; D008099:Liver / Q000201:enzymology; D010084:Oxidation-Reduction; D010944:Plants / Q000201:enzymology; D012441:Saccharomyces cerevisiae / Q000201:enzymology; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D014500:Uracil Nucleotides / Q000378:metabolism; D014539:Uridine Diphosphate Sugars / Q000138:chemical synthesis
D003837:Deoxy Sugars; D014500:Uracil Nucleotides; D014539:Uridine Diphosphate Sugars; D003847:Deoxyglucose; D000429:Alcohol Oxidoreductases; D002238:Carbohydrate Epimerases