Evaluation of oligonucleotides containing two novel 2'-O-methyl modified nucleotide monomers: a 3'-C-allyl and a 2'-O,3'-C-linked bicyclic derivative.
The two ribo-configured nucleosides 1-(3-C-allyl-2-O-methyl-beta-D-ribo-pentofuranosyl)thymine 3 and (1S,5R,6R,8R)-5-hydroxy-6-(hydroxymethyl)-1-methoxy-8-(thymin-1-yl )- 2,7-dioxabicyclo[3.3.0]octane 6 have been transformed into their corresponding phosphoramidites, 5 and 8 respectively, and used as building blocks for the synthesis of modified oligonucleotides. The oligonucleotides were shown to hybridize with decreased binding affinity towards complementary single stranded DNA and RNA.
Pfundheller
H M
HM
Department of Chemistry, University of Southern Denmark, Odense University, Denmark.
Koshkin
A A
AA
Olsen
C E
CE
Wengel
J
J
D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis*; D004277:DNA, Single-Stranded / Q000737:chemistry; D015394:Molecular Structure; D009691:Nucleic Acid Denaturation; D009692:Nucleic Acid Heteroduplexes / Q000737:chemistry; D009693:Nucleic Acid Hybridization; D009843:Oligoribonucleotides / Q000138:chemical synthesis*; D012313:RNA / Q000737:chemistry; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
D019086:Bridged Bicyclo Compounds, Heterocyclic; D004277:DNA, Single-Stranded; D009692:Nucleic Acid Heteroduplexes; D009843:Oligoribonucleotides; D012313:RNA