Oligonucleotides containing a new type of acyclic, achiral nucleoside analogue: 1-[3-hydroxy-2-(hydroxymethyl)prop-1-enyl]thymine.
An achiral, acyclic nucleoside analogue has been incorporated once or twice in oligodeoxyribonucleotides by the phosphoramidite method, and conditions found which allow deprotection of the oligonucleotides containing a sensitive modified allylic unit. The binding affinity of the modified oligonucleotides towards complementary DNA and RNA was reduced compared to unmodified DNA (DeltaT(m) -2 to -6.5 degrees C). An oligonucleotide with two modifications at the 3'-end showed considerable resistance towards cleavage with a 3'-exonuclease.
Boesen
Thomas
T
Department of Chemistry, The H. C. Ørsted Institute, University of Copenhagen, Universitetsparken 5, DK-2100 Copenhagen, Denmark.
Pedersen
Daniel Sejer
DS
Nielsen
Brian M
BM
Petersen
Asger B
AB
Henriksen
Ulla
U
Dahl
Britta M
BM
Dahl
Otto
O
D000818:Animals; D001483:Base Sequence; D018076:DNA, Complementary / Q000737:chemistry / Q000378:metabolism; D009691:Nucleic Acid Denaturation; D009692:Nucleic Acid Heteroduplexes / Q000737:chemistry; D009693:Nucleic Acid Hybridization; D009841:Oligonucleotides / Q000737:chemistry*; D010727:Phosphoric Diester Hydrolases / Q000378:metabolism; D012313:RNA / Q000737:chemistry / Q000378:metabolism; D012910:Snake Venoms; D013696:Temperature; D013941:Thymine / Q000031:analogs & derivatives* / Q000378:metabolism
D018076:DNA, Complementary; D009692:Nucleic Acid Heteroduplexes; D009841:Oligonucleotides; D012910:Snake Venoms; D012313:RNA; D010727:Phosphoric Diester Hydrolases; D013941:Thymine