The isopropoxyacetic group for convenient base protection during solid-support synthesis of oligodeoxyribonucleotides and their triester analogs.
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 hydrolyse partially or completely when standard deprotection conditions are applied.
Uznanski
B
B
Polish Academy of Sciences, Department of Bioorganic Chemistry, Lodz.
Grajkowski
A
A
Wilk
A
A
D000085:Acetates / Q000138:chemical synthesis*; D000089:Acetic Anhydrides / Q000138:chemical synthesis*; D001482:Base Composition; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D009838:Oligodeoxyribonucleotides / Q000031:analogs & derivatives / Q000138:chemical synthesis*; D010752:Phosphoramide Mustards
D000085:Acetates; D000089:Acetic Anhydrides; D009838:Oligodeoxyribonucleotides; D010752:Phosphoramide Mustards; C060405:isopropoxyacetic anhydride