Stereospecific synthesis of sugar-1-phosphates and their conversion to sugar nucleotides.
As Leloir glycosyltransferases are increasingly being used to prepare oligosaccharides, glycoconjugates, and glycosylated natural products, efficient access to stereopure sugar nucleotide donor substrates is required. Herein, the rapid synthesis and purification of eight sugar nucleotides is described by a facile 30 min activation of nucleoside 5'-monophosphates bearing purine and pyrimidine bases with trifluoroacetic anhydride and N-methylimidazole, followed by a 2 h coupling with stereospecifically prepared sugar-1-phosphates. Tributylammonium bicarbonate and tributylammonium acetate were the ion-pair reagents of choice for the C18 reversed-phase purification of 6-deoxysugar nucleotides, and hexose or pentose-derived sugar nucleotides, respectively.
Timmons
Shannon C
SC
Department of Chemistry, Dalhousie University, Halifax, Nova Scotia, Canada.
Jakeman
David L
DL
D000227:Adenine Nucleotides / Q000138:chemical synthesis / Q000737:chemistry; D002853:Chromatography, Liquid / Q000379:methods; D005643:Fucose / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D006600:Hexosephosphates / Q000138:chemical synthesis / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008860:Microscopy, Ultraviolet; D015394:Molecular Structure; D009711:Nucleotides / Q000138:chemical synthesis* / Q000737:chemistry; D012210:Rhamnose / Q000737:chemistry; D013237:Stereoisomerism; D013403:Sugar Phosphates / Q000138:chemical synthesis* / Q000737:chemistry; D014500:Uracil Nucleotides / Q000138:chemical synthesis / Q000737:chemistry
D000227:Adenine Nucleotides; D006600:Hexosephosphates; D009711:Nucleotides; D013403:Sugar Phosphates; D014500:Uracil Nucleotides; C104973:arabinose-1-phosphate; C081214:fucopyranosyl phosphate; D005643:Fucose; D012210:Rhamnose