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Issue 23, 2007
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A short and efficient synthesis of the tRNAnucleosidesPreQ0 and archaeosine

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Abstract

Modified nucleosides in tRNAs play an important role in the translational process. They fine tune the codonanticodon interactions and they influence the folding and stabilisation of the tRNA structure. Herein, we present a novel synthetic route to the highly modified nucleosidesPreQ0 and archaeosine. The synthesis involves coupling of a protected 7-cyano-7-deazaguanosine nucleobase with a TBDMS and isopropylidene protected chloro-ribose unit yielding the PreQ0nucleoside after deprotection. This PreQ0nucleoside is then used as the starting material for the synthesis of archaeosine providing the first total synthetic access to this hypermodified RNAnucleoside.

Graphical abstract: A short and efficient synthesis of the tRNAnucleosidesPreQ0 and archaeosine

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Article information


Submitted
29 Aug 2007
Accepted
27 Sep 2007
First published
12 Oct 2007

Org. Biomol. Chem., 2007,5, 3821-3825
Article type
Paper

A short and efficient synthesis of the tRNAnucleosidesPreQ0 and archaeosine

T. Brückl, F. Klepper, K. Gutsmiedl and T. Carell, Org. Biomol. Chem., 2007, 5, 3821
DOI: 10.1039/B713309J

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