Synthesis and evaluation of mimetics of UDP and UDP-alpha-D-galactose, dTDP and dTDP-alpha-D-glucose with monosaccharides replacing the key pyrophosphate unit.
A series of 5'-O-glycosyl-uridine and thymidine derivatives have been prepared as potential mimics of sugar nucleotides and nucleotide-diphosphates. These compounds proved not to be inhibitors of bovine beta-1,4-galactosyltransferase although some showed moderate inhibition of Salmonella dTDP-alpha-D-glucose 4,6-dehydratase (RmlB).
Ballell
Lluis
L
Centre for Carbohydrate Chemistry, School of Chemical Sciences and Pharmacy, University of East Anglia, Norwich, UK NR4 7TJ. r.a.field@uea.ac.uk
Young
Robert J
RJ
Field
Robert A
RA
D000818:Animals; D032701:Biomimetics; D002417:Cattle; D011756:Diphosphates / Q000737:chemistry* / Q000378:metabolism; D005947:Glucose / Q000031:analogs & derivatives* / Q000737:chemistry / Q000378:metabolism; D006836:Hydro-Lyases / Q000187:drug effects / Q000378:metabolism; D009005:Monosaccharides / Q000737:chemistry* / Q000378:metabolism; D009237:N-Acetyllactosamine Synthase / Q000187:drug effects / Q000378:metabolism; D019779:Salmonella enterica / Q000201:enzymology; D013942:Thymine Nucleotides / Q000737:chemistry* / Q000378:metabolism; D014530:Uridine Diphosphate / Q000737:chemistry* / Q000378:metabolism; D014531:Uridine Diphosphate Galactose / Q000737:chemistry* / Q000378:metabolism
D011756:Diphosphates; D009005:Monosaccharides; D013942:Thymine Nucleotides; C103522:deoxythymidine diphosphate-glucose; D014531:Uridine Diphosphate Galactose; D014530:Uridine Diphosphate; D009237:N-Acetyllactosamine Synthase; D006836:Hydro-Lyases; C022771:dTDPglucose 4,6-dehydratase; D005947:Glucose