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Nucleic Acids Research, 1985, Vol. 13, No. 18 6447-6465
© 1985

Articles

Modification of guanine bases by nucleoside phosphoramidite reagents during the solid phase synthesis of oligonucleotides

Richard T. Pon1,*, Masad J. Damha and Kelvin K. Ogilvie*

Department of Chemistry, McGill University Montreal, Quebec H3A 2K6, Canada

*To whom correspondence should be addressed

Received July 15, 1985. Revised September 6, 1985. Accepted September 6, 1985.

Nucleoside 3'-phosphoramidite and chlorophosphite reagents have been found to react with the lactam function of guanine. This reaction caused unsatisfactory results when oligodeoxyribo-nucleotides 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-pposition. A new o6-p-nitrophenylethyldeoxyguanosine phosphoramidite derivative, 8, was used to prepare sequences containing up to 24 guanine bases with greatly improved results. A hexatria-contanucleotide, d(CGCGGGGTGGAGCAGCCTGGTAGCTCGTCGGGCTCA), was also prepared using O6-protected deoxyguanosine nucleosides.

1Present Address: Dept. of Medical Biochemistry, University of Calgary, Calgary, Alberta, Canada T2N 4N1


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