Modification of guanine bases by nucleoside phosphoramidite reagents during the solid phase synthesis of oligonucleotides.
Nucleoside 3'-phosphoramidite and chlorophosphite reagents have been found to react with the lactam function of guanine. This reaction caused unsatisfactory results when oligodeoxyribonucleotides containing a large number of guanine bases were prepared in an automated solid phase synthesizer. The guanine modification is unstable, and leads to depurination and chain cleavage. This side reaction can be eliminated by protecting the O6-position. A new O6-p-nitrophenylethyldeoxyguanosine phosphoramidite derivative, 8, was used to prepare sequences containing up to 24 guanine bases with greatly improved results. A hexatriacontanucleotide, d(CGCGGGGTGGAGCAGCCTGGTAGCTCGTCGGGCTCA), was also prepared using O6-protected deoxyguanosine nucleosides.
D002855:Chromatography, Thin Layer; D004247:DNA / Q000138:chemical synthesis; D004261:DNA Replication; D004591:Electrophoresis, Polyacrylamide Gel; D006147:Guanine; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D009838:Oligodeoxyribonucleotides / Q000138:chemical synthesis*; D009943:Organophosphorus Compounds; D013329:Structure-Activity Relationship
D007202:Indicators and Reagents; D009838:Oligodeoxyribonucleotides; D009943:Organophosphorus Compounds; D006147:Guanine; D004247:DNA