title: Preparation and properties of a new type of acyclic, achiral nucleoside analogue.
abstract: Preparation of the nucleoside analogues 1 and incorporation of 1, B = T, in deoxyribooligonucleotides by the phosphoramidite method is described. A two-step deprotection procedure was developed to reduce cleavage of the modified allylic unit. The binding properties of the modified oligonucleotides towards complementary DNA and RNA has been evaluated by Tm measurements showing a deltaTm of -2 to -6.5 degrees C per modification. An oligonucleotide with two modifications at the 3'-end showed considerable resistance towards cleavage by a 3'-exonuclease. No antiviral activity against HIV-1 or HSV-1 was found for 1, B = G or T, or for any of the trihydroxy derivatives 5.
authors.affiliation: Department of Chemistry, University of Copenhagen, The H. C. Orsted Institute, Copenhagen, Denmark.
authors.forename: Thomas
authors.initials: T
authors.lastname: Boesen
authors.forename: Daniel
authors.initials: D
authors.lastname: Sejer Pedersen
authors.forename: Jacob
authors.initials: J
authors.lastname: Jensen
authors.forename: Michael T
authors.initials: MT
authors.lastname: Munck
authors.forename: Brian M
authors.initials: BM
authors.lastname: Nielsen
authors.forename: Asger B
authors.initials: AB
authors.lastname: Petersen
authors.forename: Ulla
authors.initials: U
authors.lastname: Henriksen
authors.forename: Britta M
authors.initials: BM
authors.lastname: Dahl
authors.forename: Otto
authors.initials: O
authors.lastname: Dahl
mesh_terms: D001665:Binding Sites; D004247:DNA / Q000737:chemistry; D007202:Indicators and Reagents; D008968:Molecular Conformation; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry*; D009838:Oligodeoxyribonucleotides / Q000138:chemical synthesis* / Q000737:chemistry; D012313:RNA / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D007202:Indicators and Reagents; D009705:Nucleosides; D009838:Oligodeoxyribonucleotides; D012313:RNA; D004247:DNA