title: Synthesis and incorporation of an alpha-hexofuranosyl thymidine into oligodeoxynucleotides via its two exocyclic OH-groups.
abstract: 1-(2,3-Dideoxy-3-amino-alpha-D-arabino-hexofuranosyl)thymine is considered as a conformationally restricted acyclic nucleoside using the furanose ring to link the diol backbone to the nucleobase. The appropriately substituted phosphoramidites were synthesised via 1-(5,6-di-O-acetyl-2,3-dideoxy-3-phthalimido-alpha-D-arabino-hexofuranosyl)thymine and used in oligodeoxynucleotide (ODN) synthesis. However, the binding affinity of the mixed ODNs towards complementary DNA and RNA was decreased compared to the wild-type oligos. The decrease was smaller when the monomer was inserted near the end of the sequence. The insertions into an alpha T sequence or in a beta T sequence gave nearly the same dropping in melting temperature per modification which indicates that the new nucleotide modifications behave both as alpha and beta nucleotides.
authors.affiliation: Nucleic Acid Center, Department of Chemistry, University of Southern Denmark, DK-5230, Odense M, Denmark.
authors.forename: Vyacheslav V
authors.initials: VV
authors.lastname: Filichev
authors.forename: Erik B
authors.initials: EB
authors.lastname: Pedersen
mesh_terms: D001087:Arabinonucleosides / Q000737:chemistry* / Q000378:metabolism; D001665:Binding Sites; D018076:DNA, Complementary / Q000737:chemistry; D006878:Hydroxides / Q000737:chemistry*; D015394:Molecular Structure; D009838:Oligodeoxyribonucleotides / Q000138:chemical synthesis*; D009943:Organophosphorus Compounds / Q000138:chemical synthesis*; D012313:RNA / Q000737:chemistry; D013696:Temperature; D013936:Thymidine / Q000031:analogs & derivatives* / Q000737:chemistry* / Q000378:metabolism
chemical_list: D001087:Arabinonucleosides; D018076:DNA, Complementary; D006878:Hydroxides; D009838:Oligodeoxyribonucleotides; D009943:Organophosphorus Compounds; C434331:phosphoramidite; D012313:RNA; C031356:hydroxide ion; C010032:thymine arabinoside; D013936:Thymidine