Preparation and properties of a new type of acyclic, achiral nucleoside analogue.
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.
Boesen
Thomas
T
Department of Chemistry, University of Copenhagen, The H. C. Orsted Institute, Copenhagen, Denmark.
Sejer Pedersen
Daniel
D
Jensen
Jacob
J
Munck
Michael T
MT
Nielsen
Brian M
BM
Petersen
Asger B
AB
Henriksen
Ulla
U
Dahl
Britta M
BM
Dahl
Otto
O
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
D007202:Indicators and Reagents; D009705:Nucleosides; D009838:Oligodeoxyribonucleotides; D012313:RNA; D004247:DNA