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

doi:10.1021/jo00414a028

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 journal › Article › peer-review

7 Scopus citations

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 language	English (US)
Pages (from-to)	3932-3936
Number of pages	5
Journal	Journal of Organic Chemistry
Volume	43
Issue number	20
DOIs	https://doi.org/10.1021/jo00414a028
State	Published - 1978
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

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title = "Characterization of the Products of Alkylation of 2'-Deoxyadenosine and 2'-Deoxyguanosine by Chloroethyl Ethyl Sulfide",

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.",

author = "Sack, {George H.} and Catherine Fenselau and Kan, {Man Na N.} and Kan, {Lou S.} and Wood, {Gordon W.} and Lau, {Pui Yan}",

year = "1978",

doi = "10.1021/jo00414a028",

language = "English (US)",

volume = "43",

pages = "3932--3936",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "20",

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TY - JOUR

T1 - Characterization of the Products of Alkylation of 2'-Deoxyadenosine and 2'-Deoxyguanosine by Chloroethyl Ethyl Sulfide

AU - Sack, George H.

AU - Fenselau, Catherine

AU - Kan, Man Na N.

AU - Kan, Lou S.

AU - Wood, Gordon W.

AU - Lau, Pui Yan

PY - 1978

Y1 - 1978

N2 - 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.

AB - 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.

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

Abstract

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