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. 1989 Feb 11;17(3):853–864. doi: 10.1093/nar/17.3.853

Studies on the role of tetrazole in the activation of phosphoramidites.

S Berner 1, K Mühlegger 1, H Seliger 1
PMCID: PMC331708  PMID: 2922273

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 diethoxydiisopropylaminophosphane 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.

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Selected References

These references are in PubMed. This may not be the complete list of references from this article.

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