Characterization of the Products of Alkylation of 2'-Deoxyadenosine and 2'-Deoxyguanosine by Chloroethyl Ethyl Sulfide

George H. Sack, Catherine Fenselau, Man Na N. Kan, Lou S. Kan, Gordon W. Wood, Pui Yan Lau

Research output: Contribution to journalArticlepeer-review

Abstract

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.

Original languageEnglish (US)
Pages (from-to)3932-3936
Number of pages5
JournalJournal of Organic Chemistry
Volume43
Issue number20
DOIs
StatePublished - 1978

ASJC Scopus subject areas

  • Organic Chemistry

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