Helvetica Chimica Acta p. 1106 - 1111 (1995)
Update date:2022-08-17
Topics:
Amantea
Walser
Sequin
Strazewski
The 5-methyl(15N2)[O2,O4-17O2]uridine (=(15N2)[O2,O4-17O2]ribosylthymine; 15) was synthesized and analyzed by 15N- and 17O-NMR spectroscopy. (15N2)Urea was condensed with 2,3-dibromo-2-methylpropanoyl chloride (3) and cyclized to form (15N2)thymine (5). After glycosidation, the 17O isotopes were introduced in two separate steps: hydrolytic ring opening of 2,5'-anhydro derivative 9 and hydrolysis of 3-nitro-1H-1,2,4-triazole derivative 12 with labelled water in the presence of a strong base. The 15N- and 17O-NMR spectra of 15 in phosphate-buffered water serve as references for heteronuclear NMR spectra of labelled RNA fragments.
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