title: Solid-phase synthesis of DNA fragments containing the modified base 7-hydro-8-oxo-2'-deoxyguanosine.
abstract: The 5'-(4,4'-dimethoxytrityl) protected 3'-(2-cyanoethoxy)-N,N-diisopropylphosphoramidite of 7-hydro-8-oxo-2'-deoxy-guanosine, the exocyclic amino and lactam functions of which are protected with acetyl and diphenylcarbamoyl groups, respectively, has been prepared from the 8-bromo derivatives of deoxy- and riboguanosine. This synthon, in combination with standard d-nucleoside 3'-(2-cyanoethoxy)-N,N-diisopropylphosphoramidites, was applied successfully to a solid-phase synthesis. Well-defined oligodeoxyribonucleotides containing a 7-hydro-8-oxo-2'-deoxyguanosine residue at predetermined positions were obtained after deprotection with methanolic ammonia and purification by gel filtration.
authors.affiliation: Gorlaeus Laboratories, Leiden, The Netherlands.
authors.forename: H C
authors.initials: HC
authors.lastname: Roelen
authors.forename: C P
authors.initials: CP
authors.lastname: Saris
authors.forename: H F
authors.initials: HF
authors.lastname: Brugghe
authors.forename: H
authors.initials: H
authors.lastname: van den Elst
authors.forename: J G
authors.initials: JG
authors.lastname: Westra
authors.forename: G A
authors.initials: GA
authors.lastname: van der Marel
authors.forename: J H
authors.initials: JH
authors.lastname: van Boom
mesh_terms: D000080242:8-Hydroxy-2'-Deoxyguanosine; D000641:Ammonia / Q000737:chemistry; D002850:Chromatography, Gel; D004247:DNA / Q000138:chemical synthesis* / Q000737:chemistry; D003849:Deoxyguanosine / Q000031:analogs & derivatives* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D009838:Oligodeoxyribonucleotides / Q000138:chemical synthesis* / Q000737:chemistry; D014867:Water / Q000737:chemistry
chemical_list: D009838:Oligodeoxyribonucleotides; D014867:Water; D000641:Ammonia; D000080242:8-Hydroxy-2'-Deoxyguanosine; D004247:DNA; D003849:Deoxyguanosine