The Mechanism of Cleavage Under Basic Conditions of Succinyl-Anchored Oligonucleotides
- 1 July 1998
- journal article
- research article
- Published by Taylor & Francis in Nucleosides and Nucleotides
- Vol. 17 (7) , 1177-1182
- https://doi.org/10.1080/07328319808004230
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.Keywords
This publication has 12 references indexed in Scilit:
- Criteria for the economic large scale solid-phase synthesis of oligonucleotidesTetrahedron, 1994
- An acid-labile linker for solid-phase oligoribonucleotide synthesis using Fmoc group for 5′-hydroxyl protectionTetrahedron Letters, 1993
- Improved synthesis of oligodeoxyribonucleotidesTetrahedron Letters, 1990
- The 9-fluorenylmethyloxycarbonyl group as a 5?-OH protection in oligonucleotide synthesisBiopolymers, 1989
- Solid-phase synthesis of oligoribonucleotides using 9-fluorenylmethorycarbunyl (Fmoc) for 5′-hydroryl protectionNucleic Acids Research, 1989
- A new base-stable linker for solid-phase oligonucleotide synthesisJournal of the Chemical Society, Chemical Communications, 1989
- The 9-Fluorenylmethyloxycarbonyl (Fmoc) Group as a 5′-O Base Labile Protecting Group in Solid Supported Oligonucleotide SynthesisNucleosides and Nucleotides, 1987
- Solid Phase Synthesis of DNA Under a Non-Depurinating Condition with a Base Labile 5′-Protecting Group (Fmoc) Using Phosphiteamidite ApproachNucleosides and Nucleotides, 1987
- Fluoride ion as a base in organic synthesisChemical Reviews, 1980
- Tetrabutylammonium fluoride. New reagent for the synthesis of hydantoinsThe Journal of Organic Chemistry, 1974