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. 1976 Jul;73(7):2384–2387. doi: 10.1073/pnas.73.7.2384

Comparative study by circular dichroism of the conformation of deazapurine nucleosides and that of common purine nucleosides.

D W Miles, L B Townsend, P Redington, H Eyring
PMCID: PMC430576  PMID: 1065890

Abstract

Purine nucleoside analogs modified by replacement of the nitrogen atom at the 3 position by a CH group give a characteristic circular dichroism curve that is not substantially modified by chemical substitution at the 8 position. Since it is rather well established that 8-substituted purine nucleosides are predominantly in the syn conformation in aqueous solution, it follows that the 3-deazapurine nucleosides, whether substituted at position 8 or not, also favor the syn conformation. These data are in sharp contrast to the circular dichroism data obtained on 8-halogenated and 8-alkylated derivatives of adenosine and guanosine, which give circular dichroism profiles substantially different from those obtained on the parent compounds. Certain purine-nucleoside-utilizing enzymes fail to interact effectively with either the unsubstituted 3-deaza analogs or the 8-substituted derivatives of adenosine and guanosine. The hypothesis recently given that the inactivity of the 8-substituted derivatives springs from their syn-conformational preference is tentatively accepted to explain the inactivity of the 3-deaza analogs.

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Selected References

These references are in PubMed. This may not be the complete list of references from this article.

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