Triplex forming ability of oligonucleotides containing 2'-O-methyl-2-thiouridine or 2-thiothymidine

Itaru Okamoto; Kohji Seio; Mitsuo Sekine

doi:10.1016/j.bmcl.2006.02.019

Triplex forming ability of oligonucleotides containing 2'-O-methyl-2-thiouridine or 2-thiothymidine

Bioorg Med Chem Lett. 2006 Jun 15;16(12):3334-6. doi: 10.1016/j.bmcl.2006.02.019. Epub 2006 May 2.

Authors

Itaru Okamoto¹, Kohji Seio, Mitsuo Sekine

Affiliation

¹ Department of Life Science, Tokyo Institute of Technology, Japan.

PMID: 16631365
DOI: 10.1016/j.bmcl.2006.02.019

Abstract

The triplex forming ability of oligonucleotides containing 2'-O-methyl-2-thiouridine (s2Um) and 2-thiothymidine (s2T) was studied. The UV melting experiments revealed that triplex forming oligonucleotides (TFOs) containing both s2Um or s2T stabilized significantly parallel triplexes. The main reason for stabilization of triplexes was due to the stacking effect of the 2-thiocarbonyl group. Moreover, it turned out that these modified TFOs had a high selectivity in recognition of a matched Hoogsteen base from a mismatched one.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Base Sequence
Nucleic Acid Conformation
Oligonucleotides / chemical synthesis
Oligonucleotides / chemistry*
Thiouridine / analogs & derivatives*
Thiouridine / chemistry
Thymidine / analogs & derivatives*
Thymidine / chemistry
Transition Temperature

Substances

2'-O-methyl-2-thiouridine
Oligonucleotides
Thiouridine
2-thiothymidine
Thymidine