Skip Navigation

This Article
Right arrow Print PDF (833K)
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 (16)
Right arrowRequest Permissions
Right arrow Commercial Re-use Guidelines
for Open Access NAR Content
Google Scholar
Right arrow Articles by Kuijpers, W. H. A.
Right arrow Articles by Boeckel, C. A. A.v.
Right arrow Search for Related Content
PubMed
Right arrow PubMed Citation
Right arrow Articles by Kuijpers, W. H. A.
Right arrow Articles by Boeckel, C. A. A.v.
Social Bookmarking
Add to CiteULike   Add to Connotea   Add to Del.icio.us  
What's this?

Nucleic Acids Research, 1993, Vol. 21, No. 15 3493-3500
© 1993

CHEMISTRY

The application of the AMB protective group in the solidphase synthesis of methylphosphonate DNA analogues

W. H. A. Kuijpers, E. Kuyl-Yeheskiely1, J. H.van Boom1 and C. A. A.van Boeckel

Organon International BV, PO Box 20, BH Oss 1Gorlaeus Laboratories PO Box 9502, 2300 RA Leiden, The Netherlands

Received April 8, 1993. Revised June 14, 1993. Accepted June 14, 1993.

Partially methyiphosphonate-modified oligodeoxynucleotides were synthesized on solid-phase by employing the easily removable 2-(acetoxy- methyl)benzoyl(AMB) group as base-protecting group. Although a rapid AMB deprotection can be accomplished in methanolic potassium carbonate, the lability of the methyiphosphonate linkage towards potassium carbonate/methanol excludes the use of this deprotection reagent. Thus, saturated ammonia solution in methanol was investigated as an alternative reagent for AMB removal. It is demonstrated that the combination of the AMB protective group and ammonia/methanol as deprotection reagent significantly improves the synthesis of methyl phosphonate-modifled DNA fragments. A mild overnight treatment at room temperature is sufficient for complete removal of the AMB group, whereas deprotection of conventionally protected oligonucleotides requires much longer exposure to basic conditions at elevated temperatures.


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




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.