Efficient synthesis of 2',3'-dideoxy-2'-amino-3'-thiouridine.
[reaction: see text] Metal ion rescue experiments provide a powerful approach to establish the presence and role of divalent metal ions in the biological function of RNA. The utility of this approach depends on the availability of suitable nucleoside analogues. To expand the range of this experimental strategy, we describe the first synthesis of 2',3'-dideoxy-2'-amino-3'-thiouridine (12) in 19.5% overall yield starting from 2,2'-anhydrouridine (1).
Dai
Qing
Q
Howard Hughes Medical Institute, Department of Biochemistry & Molecular Biology, The University of Chicago, 5841 South Maryland Avenue, MC 1028, Chicago, Illinois 60637, USA.
Piccirilli
Joseph A
JA
D002413:Cations, Divalent; D004220:Disulfides / Q000737:chemistry; D004229:Dithiothreitol; D007202:Indicators and Reagents; D008670:Metals; D010084:Oxidation-Reduction; D013891:Thiouridine / Q000031:analogs & derivatives* / Q000138:chemical synthesis*
C500182:2',3'-dideoxy-2'-amino-3'-thiouridine; D002413:Cations, Divalent; D004220:Disulfides; D007202:Indicators and Reagents; D008670:Metals; D013891:Thiouridine; D004229:Dithiothreitol