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Nucleic Acids Research, 1989, Vol. 17, No. 12 4863-4871
© 1989

CHEMISTRY

The isopropoxyacetic group for convenient base protection during solid-support synthesis of oligodeoxyribonucleotides and their triester analogs

Bogdan Uznanski*, Andrzej Grajkowski and Andrzej Wilk

Polish Academy of Sciences, Centre of Molecular and Macromolecular Studies, Department of Bioorganic Chemistry Boczna 5, 90–362 Lodz, Poland

*To whom correspondence should be addressed

Received November 9, 1988. Revised May 26, 1989. Accepted May 26, 1989.

Isopropoxyacetic anhydride was successfully used for protection of exoaminofunctions of 2'-deoxyadenosine, –guanosine and -cytidine. N-isopropoxyacetylated nucleosides are stable under the conditions of the synthesis of oligodeoxyribonucleotides on the solid support. Removal of N–isopropoxyacetyl is much faster than that of commonly used benzoyl or isobutyryl groups viz. it is completed within the operation of cleavage of the oligodeoxyribonucleotide from the solid support. This observation enabled synthesis of –OCH2CH3 and –OCH2CF3 triesters, which hydrolize partially or completely when standard deprotection conditions are applied.


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S. A. Surzhikov, E. N. Timofeev, B. K. Chernov, J. B. Golova, and A. D. Mirzabekov
Advanced method for oligonucleotide deprotection
Nucleic Acids Res., April 15, 2000; 28(8): e29 - e.
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