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Differentiation between isomeric phenylglycidyl ether adducts of 2′‐deoxyguanosine and 2′‐deoxyguanosine‐5′‐monophosphate using liquid chromatography/electrospray tandem mass spectrometry
Author(s) -
Lemière Filip,
Vanhoutte Koen,
Jonckers Tim,
Marek Radek,
Esmans Eddy L.,
Claeys Magda,
Van den Eeckhout Elfriede,
Van Onckelen Harry
Publication year - 1999
Publication title -
journal of mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 1076-5174
DOI - 10.1002/(sici)1096-9888(199908)34:8<820::aid-jms837>3.0.co;2-c
Subject(s) - chemistry , adduct , deoxyguanosine , electrospray , tandem mass spectrometry , mass spectrometry , alkylation , ether , nucleotide , chromatography , organic chemistry , biochemistry , gene , catalysis
The reaction between phenylglycidyl ether and 2′‐deoxyguanosine or 2′‐deoxyguanosine‐5′‐monophosphate yields a variety of different nucleoside and nucleotide adducts. The corresponding mixtures were analyzed by liquid chromatography/electrospray tandem mass spectrometry and the product ion spectra of the different isomers are discussed using the correct cone voltage and collision energy. The latter were selected by looking at the energy‐resolved spectra. From these data the formation of N7 and N2 isomers was proposed. However, detailed NMR analysis of the latter proved this isomer to be the N 1 ‐alkylated adduct. The reaction between phenylglycidyl ether and 2′‐deoxyguanosine or 2′‐deoxyguanosine‐5′‐monophosphate yields a variety of different nucleoside and nucleotide adducts. The corresponding mixtures were analyzed by liquid chromatography/electrospray tandem mass spectrometry and the product ion spectra of the different isomers are discussed using the correct cone voltage and collision energy. The latter were selected by looking at the energy‐resolved spectra. From these data the formation of N7 and N2 isomers was proposed. However, detailed NMR analysis of the latter proved this isomer to be the N 1 ‐alkylated adduct. 2′‐Deoxyguanosine‐5′‐monophosphate was alkylated by phenylglycidyl ether at the 5′‐phosphate position. If the nucleotide base moiety was alkylated, the corresponding tandem mass spectrometric data strongly suggested alkylation of N7. In the case of bis‐PGE–dGMP adduct, evidence was found for simultaneous 5′‐phosphate and N7‐alkylation.2′‐Deoxyguanosine‐5′‐monophosphate was alkylated by phenylglycidyl ether at the 5′‐phosphate position. If the nucleotide base moiety was alkylated, the corresponding tandem mass spectrometric data strongly suggested alkylation of N7. In the case of bis‐PGE–dGMP adduct, evidence was found for simultaneous 5′‐phosphate and N7‐alkylation. Copyright © 1999 John Wiley & Sons, Ltd.