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2‘-Deoxy-7-(hydroxymethyl)-7-deazaadenosine: A New Analogue to Model Structural Water in the Major Groove of DNA

Authors :
Richard I. Gumport
Jason K. Rockhill
Scott R. Wilson
Source :
Journal of the American Chemical Society. 118:10065-10068
Publication Year :
1996
Publisher :
American Chemical Society (ACS), 1996.

Abstract

A novel deoxynucleoside, 2‘-deoxy-7-(hydroxymethyl)-7-deazaadenosine, was synthesized with the intent of using the analogue to mimic the role of “structural” waters in the major groove of DNA. The target compound was synthesized in four steps starting from 2-((ethoxymethylene)amino)-5-bromo-1-(2‘-deoxy-3‘,5‘-di-O-p-toluoyl-β-d-erythro-pentofuranosyl)pyrrole-3,4-dicarbonitrile. The structure was characterized by X-ray diffraction and proton NMR spectroscopic analyses. The crystal structure shows an intramolecular hydrogen bond between an amino proton on N6 and the oxygen of the hydroxymethyl group. When superimposed onto particular adenines in the structure of the tryptophan (trp) repressor/operator complex, the analogue places the oxygen of the hydroxymethyl group very near the oxygen contributed by the water in the protein/DNA complex. This analogue may be useful for probing the role of structural waters in other specific protein/DNA complexes and in DNA bending.

Details

ISSN :
15205126 and 00027863
Volume :
118
Database :
OpenAIRE
Journal :
Journal of the American Chemical Society
Accession number :
edsair.doi...........4dbbcd12fb24a16a4bbb52987fcd3ed8
Full Text :
https://doi.org/10.1021/ja961540s