Efficient activation of nucleoside phosphoramidites with 4,5- dicyanoimidazole during oligonucleotide synthesis
Open Access
- 15 February 1998
- journal article
- research article
- Published by Oxford University Press (OUP) in Nucleic Acids Research
- Vol. 26 (4) , 1046-1050
- https://doi.org/10.1093/nar/26.4.1046
Abstract
A new activator for the coupling of phosphoramidites to the 5'-hydroxyl group during oligonucleotide synthesis is introduced. The observed time to complete coupling is twice as fast with 4, 5-dicyanoimidazole (DCI) as the activator, compared with 1 H -tetrazole. The effectiveness of DCI is thought to be based on its nucleophilicity. DCI is soluble in acetonitrile up to 1.1 M at room temperature and can be used as the sole coupling activator during routine automated solid phase synthesis of oligonucleotides. The addition of 0.1 M N -methylimidazole to 0.45 M 1 H -tetrazole also results in higher product yields during oligonucleotide synthesis than observed with 1 H -tetrazole alone.Keywords
This publication has 10 references indexed in Scilit:
- DNA aptamers block L-selectin function in vivo. Inhibition of human lymphocyte trafficking in SCID mice.Journal of Clinical Investigation, 1996
- Benzimidazolium Triflate as an Efficient Promoter for Nucleotide Synthesis via the Phosphoramidite MethodThe Journal of Organic Chemistry, 1996
- Synthesis, deprotection, analysis and purification of RNA and ribosomesNucleic Acids Research, 1995
- Kinetic Characterization of Ribonuclease-Resistant 2′-Modified Hammerhead RibozymesScience, 1991
- Studies on the role of tetrazole in the activation of phosphoramiditesNucleic Acids Research, 1989
- Highly efficient chemical synthesis of 2′-O-methyloligoribonucleotides and tetrabiotinylated derivatives; novel probes that are resistant to degradation by RNA or DNA specific nucleasesNucleic Acids Research, 1989
- 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
- Guanine modification daring chemical DNA synthesisNucleic Acids Research, 1987
- Polymer support oligonucleotide synthesis XVIII1.2): use ofβ-cyanoethyi-N,N-dialkylamino-/N-morpholino phosphoramidite of deoxynucleosides for the synthesis of DNA fragments simplifying deprotection and isolation of the final productNucleic Acids Research, 1984