Synthesis and 15N- and 17O-NMR Spectra of 5-Methyl(15N2)[O2,O4-17O2]uridine (= (15N2)[O2,O4-17O2]Ribosylthymine) |
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Authors: | Antonio Amantea Markus Walser Urs Squin Peter Strazewski |
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Institution: | Antonio Amantea,Markus Walser,Urs Séquin,Peter Strazewski |
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Abstract: | The 5-methyl(15N2)O2,O4-17O2]uridine (= (15N2)O2,O4-17O 2]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 (Fig.) of 15 in phosphate-buffered water serve as references for heteronuclear NMR spectra of labelled RNA fragments. |
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