Skip Navigation

This Article
Right arrow Print PDF (1039K)
Right arrow Alert me when this article is cited
Right arrow Alert me if a correction is posted
Services
Right arrow Email this article to a friend
Right arrow Similar articles in this journal
Right arrow Similar articles in PubMed
Right arrow Alert me to new issues of the journal
Right arrow Add to My Personal Archive
Right arrow Download to citation manager
Right arrow Search for citing articles in:
ISI Web of Science (90)
Right arrow Commercial Re-use Guidelines
for Open Access NAR Content
Google Scholar
Right arrow Articles by Wu, T.
Right arrow Articles by Pon, R. T.
Right arrow Search for Related Content
PubMed
Right arrow PubMed Citation
Right arrow Articles by Wu, T.
Right arrow Articles by Pon, R. T.
Social Bookmarking
Add to CiteULike   Add to Connotea   Add to Del.icio.us  
What's this?

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.


Add to CiteULike CiteULike   Add to Connotea Connotea   Add to Del.icio.us Del.icio.us    What's this?


This article has been cited by other articles:


Home page
 Nucleic Acids ResHome page
N. B. Gaied, N. Glasser, N. Ramalanjaona, H. Beltz, P. Wolff, R. Marquet, A. Burger, and Y. Mély
8-vinyl-deoxyadenosine, an alternative fluorescent nucleoside analog to 2'-deoxyribosyl-2-aminopurine with improved properties
Nucleic Acids Res., February 17, 2005; 33(3): 1031 - 1039.
[Abstract] [Full Text] [PDF]

Home page
 ScienceHome page
D. Pei, H. Ulrich, and P. Schultz
A combinatorial approach toward DNA recognition
Science, September 20, 1991; 253(5026): 1408 - 1411.
[Abstract] [PDF]


Disclaimer:
Please note that abstracts for content published before 1996 were created through digital scanning and may therefore not exactly replicate the text of the original print issues. All efforts have been made to ensure accuracy, but the Publisher will not be held responsible for any remaining inaccuracies. If you require any further clarification, please contact our Customer Services Department.