Efficient Synthesis of 1-Deaza-6-methoxypurine-N9-β-2′-deoxyribonucleoside and Related DNA Building Blocks

Abstract

An improved synthesis of the 2′-deoxyribonucleoside containing 1-deaza-6-methoxypurine as artificial nucleobase is described. By optimizing the conditions for the deprotection of p-toluoyl-protected 1-deaza-6-nitropurine 2′-deoxyribonucleoside, the isolated yield of the title compound could be increased from 15% to 90%. In addition, the synthesis and characterization of the corresponding 5′-(4,4′-dimethoxytrityl) (DMT) protected phosphoramidite, a potentially useful building block for the synthesis of artificial oligonucleotides, is reported. The title compound offers interesting hydrogen bond donor and metal-binding properties for its application in metal-mediated base pairs.

Keywords:

• 2′-Deoxyribonucleoside
• methoxy denitration
• purine

ACKNOWLEDGMENTS

Generous financial support by the Deutsche Forschungsgemeinschaft (MU1750/2-1, IRTG 1444) is gratefully acknowledged. We thank Fabian-Alexander Polonius for help with the initial characterization of the reaction products.