The solid-phase synthesis of 2-5-linked oligoriboadenylates containing 8-bromoadenine |
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Authors: | Krystyna B Lesiak Bogdan Uznanski Paul F Torrence |
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Institution: | 1. Section on Biomedical Chemistry,Laboratory of Medicinal Chemistry, National Institute of Diabetes and Digestive and Kidney Diseases, National Institutes of Health, 20892, Bethesda, MD 2. Center of Molecular and Macromolecular Studies, Polish Academy of Sciences, 90-363, Lodz, Poland
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Abstract: | To increase the accessibility of 8-bromo-2′,5′-oligoadenylates, we developed a synthesis of 2′-5′-linked oligoriboadenylates containing varying numbers of 8-bromoadenosine residues based on the use of a CPG-LCA solid support and the phosphoramidite approach. Although N6benzoyl protection was satisfactory for incorporation of nonmodified adenine residues into 2′,5′-oligonucleotides, the effective incorporation of 8-bromoadenine into such 2′,5′-linked oligomers required use of a non acyl protecting group. Amidine protection of the purine exocyclic amino function proved compatible with all aspects of the phophoramidite approach and with the hydroxyl protection groups employed. |
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