The mechanism of cleavage under basic conditions of succinyl-anchored oligonucleotides

Article abstract of DOI:10.1080/07328319808004230

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 succinamide 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.

Full text of DOI:10.1080/07328319808004230

Nucleosides and Nucleotides
ISSN: 0732-8311 (Print) (Online) Journal homepage: http://www.tandfonline.com/loi/lncn19
The Mechanism of Cleavage Under Basic
Conditions of Succinyl-Anchored Oligonucleotides
Yolanda Palom , Anna Grandas & Enrique Pedroso
To cite this article: Yolanda Palom , Anna Grandas & Enrique Pedroso (1998) The Mechanism
of Cleavage Under Basic Conditions of Succinyl-Anchored Oligonucleotides, Nucleosides and
Nucleotides, 17:7, 1177-1182, DOI: 10.1080/07328319808004230
To link to this article: http://dx.doi.org/10.1080/07328319808004230
Published online: 21 Aug 2006.
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Date: 08 June 2016, At: 09:05