CHARACTERIZATION OF PRODUCTS OF ALKYLATION OF 2'-DEOXYADENOSINE AND 2'-DEOXYGUANOSINE BY CHLOROETHYL ETHYL SULFIDE

被引:9
作者
SACK, GH
FENSELAU, C
KAN, MNN
KAN, LS
WOOD, GW
LAU, PY
机构
[1] JOHNS HOPKINS MED INST, BALTIMORE, MD 21205 USA
[2] UNIV WINDSOR, DEPT CHEM, WINDSOR N9B 3P4, ONTARIO, CANADA
关键词
D O I
10.1021/jo00414a028
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
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. © 1978, American Chemical Society. All rights reserved.
引用
收藏
页码:3932 / 3936
页数:5
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