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

The natural products PreQ1, PreQ0, 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 c...

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Bibliographic Details
Published in:European Journal of Organic Chemistry 2010, Vol.2010 (34), p.6517-6519
Main Authors: Brückl, Tobias, Thoma, Ines, Wagner, Andreas J., Knochel, Paul, Carell, Thomas
Format: Review
Language:English
Subjects:
Carbohydrates. Nucleosides and nucleotides
Chemistry
Exact sciences and technology
Grignard reaction
Natural products
Nucleosides, nucleotides and oligonucleotides
Nucleo­sides
Organic chemistry
Preparations and properties
tRNA
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Summary:The natural products PreQ1, PreQ0, 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. PreQ1, PreQ0, and archaeosine were prepared from a common iododeazaguanosine intermediate by an efficient and divergentroute. This approach was facilitated by the development of a novel, functional group tolerating Turbo‐Grignard reaction.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201000987