title: Enzyme-catalyzed synthesis of furanosyl nucleotides.
abstract: A bacterial alpha-d-glucopyranosyl-1-phosphate thymidylyltransferase was found to couple four hexofuranosyl-1-phosphates, as well as a pentofuranosyl-1-phosphate, with deoxythymidine 5'-triphosphate, providing access to furanosyl nucleotides. The enzymatic reaction mixtures were analyzed by electrospray ionization mass spectrometry and NMR spectroscopy to determine the anomeric stereochemistry of furanosyl nucleotide products. This is the first demonstration of a nucleotidylyltransferase discriminating between diastereomeric mixtures of sugar-1-phosphates to produce stereopure, biologically relevant furanosyl nucleotides.
authors: Department of Chemistry, Dalhousie University, Halifax, Nova Scotia, Canada.
authors: Shannon C
authors: SC
authors: Timmons
authors: Joseph P M
authors: JP
authors: Hui
authors: Jessica L
authors: JL
authors: Pearson
authors: Pauline
authors: P
authors: Peltier
authors: Richard
authors: R
authors: Daniellou
authors: Caroline
authors: C
authors: Nugier-Chauvin
authors: Evelyn C
authors: EC
authors: Soo
authors: Ray T
authors: RT
authors: Syvitski
authors: Vincent
authors: V
authors: Ferrières
authors: David L
authors: DL
authors: Jakeman
mesh_terms: D002384:Catalysis; D015394:Molecular Structure; D009711:Nucleotides / Q000138:chemical synthesis* / Q000737:chemistry; D009713:Nucleotidyltransferases / Q000378:metabolism*; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D009711:Nucleotides; C523475:Glc-1-P thymidyltransferase, Streptomyces globisporus; D009713:Nucleotidyltransferases