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Chemical transformation/derivatization of O6-methyl- and O6-(hydroxyethyl)guanine for detection by GC-EC/MS.

Authors
Chiu-CS; Saha-M; Abushamaa-A; Giese-RW
Source
Anal Chem 1993 Nov; 65(21):3071-3075
NIOSHTIC No.
00217284
Abstract
A technique for derivatizing O6-alkyl and O6-(hydroxyalkyl) guanines prior to detection by gas chromatography/electron capture/mass spectrometry was developed. The procedure was developed using O6- methylguanine (O6MeGua) and O6-(2'-hydroxyethyl)guanine (O6HOEtGua) as representative analytes. O6MeGua and O6OHEtGua were reacted with sodium-nitrite and tetrafluoroboric-acid to produce O6 substituted hypoxanthine derivatives. The hypoxanthine derivatives were subsequently reacted with pentafluorobenzyl-bromide to produce a series of pentafluorobenzyl ethers, pentafluorobenzyl-methyl ethers, pentafluorobenzyl-tert-butyl ethers, benzoyl-pentafluorobenzyl esters, and pivalyl-pentafluorobenzyl esters. The pentafluorobenzyl- tert-butyl ethers were selected as the best choice for quantitation by gas chromatography electron capture mass spectrometry (GC/EC/MS). The pentafluorobenzyl-tert-butyl ethers could be quantitated with detection limits of 1.16 and 1.24 picograms (pg). The detection limits for the pivalyl-pentafluorobenzyl derivatives were 1.27 and 1.31pg. The authors conclude that the procedure successfully converts O6meGua and O6OHETGua into derivatives that can be easily quantitated by GC/EC/MS.
Keywords
NIOSH-Publication; NIOSH-Grant; Grants-other; DNA-adducts; Analytical-methods; Nucleosides; Chemical-reactions; Gas-chromatography; Mass-spectrometry
Contact
Medicinal Chemistry Northeastern University 360 Huntington Avenue Boston, MA 02115
CODEN
ANCHAM
Publication Date
19931101
Document Type
Journal Article
Funding Amount
433637.00
Funding Type
Grant
Fiscal Year
1994
NTIS Accession No.
NTIS Price
Identifying No.
Grant-Number-R01-OH-02792
Issue of Publication
21
ISSN
0003-2700
Priority Area
Other Occupational Concerns; Grants-other
Source Name
Analytical Chemistry
State
MA
Performing Organization
Northeastern University, Boston, Massachusetts
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