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Efficient Synthesis of Deazaguanosine-Derived tRNA Nucleosides PreQ(0), PreQ(1), and Archaeosine Using the Turbo-Grignard Method

  作者 BRUECKL TOBIAS; THOMA INES; WAGNER ANDREAS J; KNOCHEL PAUL; CARELL THOMAS  
  选自 期刊  European Journal of Organic Chemistry;  卷期  2010年-34;  页码  6517-6519  
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[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.

 
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