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Synthesis and 15N- and 17O-NMR Spectra of 5-Methyl(15N2)[O2,O4-17O2]uridine (= (15N2)[O2,O4-17O2]Ribosylthymine)

✍ Scribed by Antonio Amantea; Markus Walser; Urs Séquin; Peter Strazewski

Publisher
John Wiley and Sons
Year
1995
Tongue
German
Weight
447 KB
Volume
78
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

The 5‐methyl(^15^N~2~)[O^2^,O^4^‐^17^O~2~]uridine (= (^15^N~2~)[O^2^,O^4^‐^17^O ~2~]ribosylthymine; 15) was synthesized and analyzed by ^15^N‐ and ^17^O‐NMR spectroscopy. (^15^N~2~)Urea was condensed with 2,3‐dibromo‐2‐methylpropanoyl chloride (3) and cyclized to form (^15^N~2~)thymine (5). After glycosidation, the ^17^O isotopes were introduced in two separate steps: hydrolytic ring opening of 2,5′‐anhydro derivative 9 and hydrolysis of 3‐nitro‐1__H__‐1,2,4‐triazole derivative 12 with labelled water in the presence of a strong base. The ^15^N‐ and ^17^O‐NMR spectra (Fig.) of 15 in phosphate‐buffered water serve as references for heteronuclear NMR spectra of labelled RNA fragments.

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