Efficient Synthesis of Deazaguanosine-Derived tRNA Nucleosides PreQ0, PreQ1, and Archaeosine Using the Turbo-Grignard Method

被引：14

作者：

Brueckl, Tobias ^{[1
]}

Thoma, Ines ^{[1
]}

Wagner, Andreas J. ^{[1
]}

Knochel, Paul ^{[1
]}

Carell, Thomas ^{[1
]}

机构：

[1] Univ Munich, Dept Chem, Ctr Integrat Prot Sci CiPSM, D-81377 Munich, Germany

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 2010卷 / 34期

关键词：

Grignard reaction; Nucleosides; tRNA; Natural products; C-H ARYLATION; HYPERMODIFIED NUCLEOSIDE; QUEUINE; BASE; QUEUOSINE; PURINES; RIBONUCLEOSIDES; QUANTIFICATION; GLYCOSYLATION; BIOSYNTHESIS;

D O I：

10.1002/ejoc.201000987

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The natural products PreQ(1), PreQ(0), and archaeosine are deazaguanosine-derived natural products of immense biological importance. All three are critical components of tRNAs and, as such, are involved in decoding genetic information. We were able to consolidate and shorten the syntheses of all three compounds by using a novel Turbo-Grignard-based approach. The reported iodine/magnesium exchange followed by a Grignard reaction with the deazaguanosine skeleton showed a high tolerance towards important functional groups such as esters and amides.

引用

页码：6517 / 6519

页数：3

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