Journal
RSC ADVANCES
Volume 4, Issue 61, Pages 32588-32593Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c4ra04784b
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- NSF
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A concise synthesis of both C5' diastereomers of 5'-(hydroxymethyl)-6,5'-cyclo-2',5'-dideoxyuridine is presented. Individual crystal structures of the fully deprotected S- and R-stereoisomers indicate that the addition of a methylene group between the C5' and O5' positions of 6,5'-cyclo-2'-deoxyuridine increases the distance between the nucleobase and backbone. The resulting nucleosides adopt a conformation that more closely mimics A-form rather than B-form nucleotides. Nucleotides of 5'(R)-(hydroxymethyl)-6,5'-cyclo-2',5'-dideoxyuridine were successfully incorporated into DNA oligonucleotides during automated synthesis, but full-length oligonucleotides were not obtained after post-synthetic cleavage from the solid support due to a base-catalyzed strand cleavage at the site of insertion.
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