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Nucleic Acids Research, 1989, Vol. 17, No. 9 3501-3517
© 1989

CHEMISTRY

Prevention of chain cleavage in the chemical synthesis of 2'-silylated oligoribonucleotides

Taifeng Wu, Kelvin K. Ogilvie1,* and Richard T. Pon2

Department of Chemistry, McGill University 801 Sherbrooke St. W., Montreal, Quebec H3A 2K6 1Acadia University Wolfville, Nova Scotia B0P 1H0 2Department of Medical Biochemistry, University of Calgary Calgary, Alberta T2N 4N1, Canada

*To whom correspondence should be addressed

Received March 2, 1989. Accepted April 12, 1989.

Strong aqueous ammonium hydroxide used to remove N-acyl protecting groups from synthetic oligoribonucleotides causes removal of some alkylsilyl protecting groups from 2'-hydroxyls and leads to chain cleavage. This problem is most severe when 30% ammonium hydroxide is used and substantially reduced but still detectable when 3:1 ammonium hydroxide-ethanol is used. We have virtually eliminated this unwanted cleavage by incorporating the labile phenoxyacetyl amino protecting group on adenosine and guanosine. The N-benzoyl protecting group remains adequate for cytidine nucleosides. Synthetic oligoribonucleotides containing these N-acylated nucleosides and 2'-t-butyldimethylsilyl or 2'-triisopropylsilyl protecting groups can be deacylated by room temperature treatment in saturated anhydrous methanolic ammonia (8-12 h) without causing any detectable chain cleavage.


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