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

• Published in: Nucleic acids research Vol. 17; no. 12; pp. 4863 - 4872
• Main Authors: Uznanski, B, Grajkowski, A, Wilk, A
• Format: Journal Article
• Language: English
• Published: 01-01-1989
• ISSN: 0305-1048

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 oligodeoxy-ribonucleotides 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 oligodeoxy-ribonucleotide from the solid support. This observation enabled synthesis of -OCH sub(2)CH sub(3) and -OCH sub(2)CF sub(3) triesters, which hydrolyze partially or completely when standard deprotection conditions are applied.