Timmons Shannon C, Hui Joseph P M, Pearson Jessica L, Peltier Pauline, Daniellou Richard, Nugier-Chauvin Caroline, Soo Evelyn C, Syvitski Ray T, Ferrières Vincent, Jakeman David L
Department of Chemistry, Dalhousie University, Halifax, Nova Scotia, Canada.
Org Lett. 2008 Jan 17;10(2):161-3. doi: 10.1021/ol7023949. Epub 2007 Dec 20.
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.
发现一种细菌α-D-吡喃葡萄糖基-1-磷酸胸苷酰转移酶能将四种呋喃己糖基-1-磷酸以及一种呋喃戊糖基-1-磷酸与脱氧胸苷5'-三磷酸偶联，从而获得呋喃糖核苷酸。通过电喷雾电离质谱和核磁共振光谱对酶促反应混合物进行分析，以确定呋喃糖核苷酸产物的异头立体化学。这是首次证明核苷酸转移酶能够区分糖-1-磷酸的非对映异构体混合物，以产生立体纯的、具有生物学相关性的呋喃糖核苷酸。
