Studies on the role of tetrazole in the activation of phosphoramidites
Open Access
- 11 February 1989
- journal article
- research article
- Published by Oxford University Press (OUP) in Nucleic Acids Research
- Vol. 17 (3) , 853-864
- https://doi.org/10.1093/nar/17.3.853
Abstract
The mechanism of the tetrazole-activated coupling step in the synthesis of oligonucleotides via phosphoramidites is studied with the help of model reactions: Treatment of diethoxydiisopro-pylaminophosphane with two equivalents of tetrazole resulted in a diethoxy-tetrazolophosphane, whose (31P)-NMR shift of 126 ppm is identical with the signal observed during internucleotide bond formation. A series of different related diethoxy-phosphorous-acid derivatives were also synthesized; their (31P)-NMR signals between 123.9 and 130.8 ppm are additional evidence for the intermediacy of a tetrazolide species. Further NMR investigations with more basic azoles showed that tetrazole is also active as a proton donor.This publication has 3 references indexed in Scilit:
- Mechanistic studies on the phosphoramidite coupling reaction in oligonucleotide synthesis. I. Evidence for nudeophilic catalysis by tetrazole and rate variations with the phosphorus substituentsNucleic Acids Research, 1987
- Modification of guanine bases by nucleoside phosphoramidite reagents during the solid phase synthesis of oligonucleotidesNucleic Acids Research, 1985
- Synthesis of deoxyoligonucleotides on a polymer supportJournal of the American Chemical Society, 1981