130277-32-6Relevant articles and documents
Synthesis of a Novel Coumarin C-Riboside as a Photophysical Probe of Oligonucleotide Dynamics
Coleman, Robert S.,Madaras, Mihaela L.
, p. 5700 - 5703 (1998)
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Synthesis of a dA-dT base pair analogue and its effects on DNA-ligand binding
Lan, Tao,McLaughlin, Larry W.
, p. 198 - 210 (2007/10/03)
Two nucleoside derivatives containing the base analogues 3-deazaadenine and 3-methyl-2-pyridone have been prepared as analogues of dA and dT, respectively. After conversion into the appropriately protected phosphoramidites, DNA sequences were prepared with site-specifically placed analogues. When present in a duplex DNA sequence, the analogues result in the deletion of one or both of the hydrogen bonding functional groups (the N3-nitrogen of dA and the O2-carbonyl of dT) present in the minor groove. Binding by two ligands, 4′,6-diamidine-2-phenyl indole (DAPI) and Hoechst 33258 in the minor groove has been probed using a variety of DNA sequences. These sequences contain a d(GAATTC)2 core with analogue nucleosides substituted for one or more of the dA and dT residues. DAPI bound strongly to any sequence that contained both O2-carbonyls of the central two dT residues. The presence of a dc3A residue did in some cases enhance binding. With one of the central O2-carbonyls deleted, the binding was noticeably reduced, and with both absent, no significant binding could be detected. Similar although less dramatic results were observed with Hoechst 33258 binding to analogue sequences.
Facile preparation of protected furanoid glycals from thymidine
Cameron, Melissa A.,Cush, Sarah B.,Hammer, Robert P.
, p. 9065 - 9069 (2007/10/03)
The synthesis of O-silyl- and O-acyl-protected furanose glycals from free thymidine was investigated. The method of glycal formation reported by Pedersen et al. was successfully expanded to include 5-ester (toluoyl) protected glycals as well as various combinations of 5'-ester and 3- and 5- tert-butyldimethylsilyl and tert-butyldiphenylsilyl protection. Gram quantities of furanoid glycals can be prepared in a few days in two-four steps in overall yields ranging from 17 to 80%.