Alkylation of 2'-deoxyadenosine by 2-chloroethyl ethyl sulfide (CEES) in aqueous solutions at pH 6.0 and 25°C led to two products. These have been isolated and characterized on the basis of mass spectrometry, nuclear magnetic resonance spectroscopy, ultraviolet spectroscopy as 2'-deoxy-1-[2-(ethylthio)ethyl]adenosine and 2'-deoxy-N6-[2-(ethylthio)ethyl]adenosine. The products formed from 2'-deoxyguanosine under these same conditions were identified as 2'-deoxy-7-[2-(ethylthio)ethyl]guanosine and 2'-deoxy-N2-[2-(ethylthio)ethyl]guanosine, the corresponding pair of deribosylated alkylated purines.
ASJC Scopus subject areas
- Organic Chemistry