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

Details

• Personal Author:
  Abushamaa A ; Chiu CS ; Giese RW ; Saha M
• Description:
  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. [Description provided by NIOSH]
• Subjects:
  Chemistry Mass Spectrometry Occupational Health Safety
• Keywords:
  Analytical-methods Chemical-reactions DNA-adducts Gas-chromatography Grants-other Mass-spectrometry NIOSH-Grant NIOSH-Publication Nucleosides
• ISSN:
  0003-2700
• Document Type:
  Text
• Funding:
  Grant
• Genre:
  Journal Article
• Place as Subject:
  Massachusetts ; OSHA Region 1
• CIO:
  National Institute for Occupational Safety and Health (NIOSH)
• Topic:
  Workplace Safety & Health
• Location:
  North America
• Volume:
  65
• Issue:
  21
• NIOSHTIC Number:
  nn:00217284
• Citation:
  Anal Chem 1993 Nov; 65(21):3071-3075
• Contact Point Address:
  Medicinal Chemistry Northeastern University 360 Huntington Avenue Boston, MA 02115
• Federal Fiscal Year:
  1994
• NORA Priority Area:
  Other Occupational Concerns ; Grants Other
• Performing Organization:
  Northeastern University, Boston, Massachusetts
• Peer Reviewed:
  True
• Start Date:
  19910101
• Source Full Name:
  Analytical Chemistry
• End Date:
  19961130
• Collection(s):
  National Institute for Occupational Safety and Health
• Main Document Checksum:
  urn:sha-512:69d334da40640f0802f0879f8f2d7fe71db00329ab05198a8699566eac4ec0717edae9580e3ed4d731592240c9732e69720bf9e2228e01788d66ea7f83396f47
• Download URL:
  https://stacks.cdc.gov/view/cdc/204318/cdc_204318_DS1.pdf
• File Type:
  [PDF - 681.73 KB ]