Synthesis of Oligonucleotides Containing 2?-Deoxyisoguanosine and 2?-Deoxy-5-methylisocytidine Using Phosphoramidite Chemistry
| Autor: | J. David Rozzell, Thomas R. Battersby, J. T. Kodra, Simona C. Jurczyk, Steven A. Benner |
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| Rok vydání: | 1998 |
| Předmět: |
Phosphoramidite
Oligonucleotide Chemistry Stereochemistry Organic Chemistry Oligonucleotide synthesis Biochemistry Combinatorial chemistry Catalysis Inorganic Chemistry 2'-deoxyisoguanosine 2'-deoxy-5-methylisocytidine Drug Discovery Standard protocol Moiety Physical and Theoretical Chemistry Protecting group |
| Zdroj: | Helvetica Chimica Acta. 81:793-811 |
| ISSN: | 1522-2675 0018-019X |
| DOI: | 10.1002/hlca.19980810502 |
| Popis: | The synthesis of oligonucleotides containing 2′-deoxy-5-methylisocytidine and 2′-deoxyisoguanosine using phosphoramidite chemistry in solid-phase oligonucleotide synthesis is described. Supporting previous observations, the N,N-diisobutylformamidine moiety was found to be a far superior protecting group than N-benzoyl for 2′-deoxy-5-methylisocytidine. 2′-Deoxy-N2-[(diisobutylamino)methylidene]-5′-(4,4′-dimethoxytityl)-5-methylisocytidine 3′-(2-cyanoethyl diisopropylphosphoramidite) (1c) incorporated multiple consecutive residues during a standard automated synthesis protocol with a coupling efficiency > 99% according to dimethoxytrityl release. Extending coupling times of the standard protocol to ≥ 600s using 2′-deoxy-N6-[(diisobutylamino)methylidene]-5′-O-(dimethoxytrityl)-O2-(diphenylcarbamoyl)isoguanosine, 3′-(2-cyanoethyl diisopropylphosphoramidite) (7e) led to successful incorporation of multiple consecutive 2′-deoxyisoguanosine bases with a coupling efficiency > 97% according to dimethoxytrityl release. |
| Databáze: | OpenAIRE |
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