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Synthesis of (15N2)[17O]Urea, (15N2)[O2, O4-17O2]Uridine, and (15N3)[O2-17O]Cytidine

✍ Scribed by Antonio Amantea; Matthias Henz; Peter Strazewski

Publisher
John Wiley and Sons
Year
1996
Tongue
German
Weight
771 KB
Volume
79
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

A general synthetic approach for the synthesis of ^15^N‐ and ^17^O‐doubly labelled pyrimidine nucleosides is described. The ^15^N isotopes in uridine and the ^17^O isotope in the urea‐derived carbonyl group of uridine and cytidine originate from (^15^N~2~)[^17^O]urea (5) which was synthesized from ^15^NH~4~Cl, thiophosgene (1), and H~2~[^17^O]. The third ^15^N isotope of cytidine in 4‐position stems from the substitution of the 1,2,4‐triazole moiety of (^15^N~2~)[O^2^‐^17^O]uridine derivative 8a/b with ^15^NH~4~OH. Hydrolysis of the same key intermediate 8a/b with Na[^17^O]H/H~2~[^17^O] introduced the second ^17^O isotope into the 4‐position of uridine. The ^15^N‐ and ^17^O‐NMR spectra of the target compounds 12 and 14 in phosphate‐buffered H~2~O serve as references for heteronuclear NMR spectra of labelled RNA fragments.

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