1,N⁶‐Etheno‐2′‐doexytubercidin and Pyrrolo‐C: Synthesis, Base Pairing, and Fluorescence Properties of 7‐Deazapurine Nucleosides and Oligonucleotides.

Abstract

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1,N6-Etheno-7-deaza-2,8-diazaadenosine: syntheses, properties and conversion to 7-deaza-2,8-diazaadenosine

“…1b This problem is circumvented by the use of 1,N 6 etheno-7-deaza-2 -deoxyadenosine (2) (purine numbering is used in the results and discussion sections, except otherwise stated) being stable under acidic and alkaline conditions due to the replacement of the purine by the pyrrolo [2,3-d]pyrimidine system. 4 Among the various etheno nucleosides, 2-azapurine derivatives, such as 1,N 6 -etheno-2-azaadenosine (2-aza-e-adenosine, 3a) 5a,b as well as its 2 -deoxy derivative 3b 5c have been incorporated into RNA and DNA chemically or enzymatically. 1b,1c, 6 From fluorescence studies performed on those nucleosides it became obvious that the fluorescence emission maximum of compound 3a (495 nm) is bathochromically shifted compared to 1b (415 nm)-both measured at pH 7.0 in aq.…”