Nitromethane as a scavenger of acrylonitrile in the deprotection of synthetic oligonucleotides |
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Authors: | Tadashi Umemoto |
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Institution: | Department of Medical Genome Sciences, Graduate School of Frontier Sciences, The University of Tokyo, Bioscience Bldg 702, 5-1-5 Kashiwanoha, Kashiwa-shi, Chiba 277-8562, Japan |
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Abstract: | A novel deprotection procedure for synthetic oligonucleotides was developed to prevent nucleobase alkylation. Acrylonitrile, a side product of the deprotection of a 2-cyanoethyl phosphate protecting group and which causes nucleobase alkylation, was found to be trapped by the addition of some acidic compounds, which generate a carbanion species under the conventional deprotection conditions using aqueous NH3. The 2-cyanoethylation of thymidine was inhibited effectively in the presence of nitromethane. |
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Keywords: | Oligonucleotide Chemical synthesis 2-Cyanoethylation |
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