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Preparation of deuterium-labeled nucleosides by platinum-catalyzed exchange and reduction

✍ Scribed by T. Kinoshita; Karl H. Schram; James A. McCloskey

Publisher
John Wiley and Sons
Year
1982
Tongue
French
Weight
345 KB
Volume
19
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

Selective incorporation of deuterium by platinum‐catalyzed exchange for six ribonucleosides and two 2′‐deoxyribonucleosides has been studied as a function of catalyst/substrate ratio, temperature, time and concentration. In addition to exchange of carbon‐bound hydrogens in purines, pyrimidines and pyrrolo[2,3‐d]‐pyrimidines, reactions involving D~2~‐saturated D~2~O as solvent were used to effect extensive exchange of ribose hydrogens, principally at C‐2′. Reduction‐exchange of uridine was used to prepare 5,6‐dihydrouridine‐5,5,6,6,‐d~4~, and 4‐amino‐5,6‐dihydro‐7‐(β‐D‐ribofuranosyl)pyrrolo[2,3‐d] pyrimidine‐2,5,5,6,6‐d~5~ from tubercidin. Sites and extent of deuteration were determined by mass spectrometry and proton magnetic resonance.

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