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Original Articles

The Mechanism of Cleavage Under Basic Conditions of Succinyl-Anchored Oligonucleotides

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Pages 1177-1182 | Published online: 21 Aug 2006
 

Abstract

Studies with a model compound provide direct evidence that cleavage of succinyl-anchored oligonucleotides takes place by intramolecular nucleophilic attack of the conjugate base of the succinamide at the ester carbonyl group. An N-substituted succinimide is exclusively formed with piperidine, DBU and TBAF, but when ammonia is used-this general mechanism seems to coexist with ammonolysis of the succinate ester. Cleavage with TBAF is extremely fast.

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