Efficient synthesis of the tRNA nucleoside preQ0, 7-cyano-7-deazaguanosine, via microwave-assisted iodo→carbonitrile exchange.
The naturally occurring tRNA nucleoside preQ(0), 7-cyano-7-deazaguanosine, which is a central intermediate for other natural occurring 7-deazapurine nucleosides was synthesized via a copper(I)-ion-mediated iodo→carbonitrile exchange. The reaction was performed on the easily accessible 7-iodo-7-deazaguanosine under microwave conditions. The overall reaction yield was 30% starting with the glycosylation reaction of the nucleobase. Corresponding 2'-deoxyribonucleosides were prepared following the same route.
Ming
Xin
X
Laboratory of Bioorganic Chemistry and Chemical Biology, Center for Nanotechnology, Heisenbergstrasse 11, D-48149 Münster, Germany.
Seela
Frank
F
D003300:Copper / Q000737:chemistry; D006031:Glycosylation; D006151:Guanosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008872:Microwaves; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D009704:Nucleoside Q / Q000138:chemical synthesis* / Q000737:chemistry; D012343:RNA, Transfer / Q000138:chemical synthesis* / Q000737:chemistry
C556329:7-cyano-7-deazaguanosine; C556328:7-iodo-7-deazaguanosine; D009570:Nitriles; D006151:Guanosine; D009704:Nucleoside Q; D003300:Copper; D012343:RNA, Transfer