Predicted Exocyclic Amino Group Alkylation of 2‘-Deoxyadenosine and 2‘-Deoxyguanosine by the Isopropyl Cation
- 6 May 2000
- journal article
- research article
- Published by American Chemical Society (ACS) in Chemical Research in Toxicology
- Vol. 13 (6) , 431-435
- https://doi.org/10.1021/tx000059j
Abstract
Diisopropyltriazene in aqueous 10% acetonitrile (pH 7.0 +/- 0.4) yields N-6-isopropyl-2'-deoxyAdo as the predominant product and N-2-isopropyl-2'-deoxyGuo in yields comparable with the O-6 adduct in reactions with 2'-deoxyAdo and 2'-deoxyGuo, respectively. These observations are inconsistent with what is expected on the basis of the regnant hypothesis concerning factors that determine atom site selectivity in diazonium ion-mediated alkylations. An alternative explanation based on the fleeting existence of the reactive intermediates involved is consistent with these observations.This publication has 13 references indexed in Scilit:
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