A short and efficient synthesis of the tRNA nucleosides PreQ0 and archaeosine

被引：15

作者：

Bruckl, Tobias ^{[1
]}

Klepper, Florian ^{[1
]}

Gutsmiedl, Katrin ^{[1
]}

Carell, Thomas ^{[1
]}

机构：

[1] Univ Munich, D-81377 Munich, Germany

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2007年 / 5卷 / 23期

关键词：

D O I：

10.1039/b713309j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Modified nucleosides in tRNAs play an important role in the translational process. They. ne tune the codon-anticodon interactions and they influence the folding and stabilisation of the tRNA structure. Herein, we present a novel synthetic route to the highly modified nucleosides PreQ(0) 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 PreQ(0) nucleoside after deprotection. This PreQ(0) nucleoside is then used as the starting material for the synthesis of archaeosine providing the first total synthetic access to this hypermodified RNA nucleoside.

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收藏

页码：3821 / 3825

页数：5

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