ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
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.
Additional Material:
4 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19980810502
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