Protolytic and nucleophilic role of phosphoramidite method promoters




Nurminen EJ, Mattinen JK, Lonnberg H

2002

Collection Symposium Series

CHEMISTRY OF NUCLEIC ACID COMPONENTS

COLL SYMPOS SERIES

5

129

134

6

80-86241-16-5



The effect of promoters applied in phosphoramidite alcoholysis is based on both acid and nucleophilic catalysis. Observed Bronsted alpha values 0.6-0.9 and beta(nucl) value of 0.2 emphasise the importance of the acidic contribution. Still, highly nucleophilic azole activators of moderate acidity have shown excellent reactivity and should be considered as most promising alternatives to tetrazole as activators in oligonucleotide synthesis.



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