Synthesis of 6-N-(benzothiazol-2-yl)deoxyadenosine and its exciton-coupled circular dichroism

Yoshiaki Masaki; Akihiro Ohkubo; Kohji Seio; Mitsuo Sekine

doi:10.1016/j.bmc.2009.12.009

Synthesis of 6-N-(benzothiazol-2-yl)deoxyadenosine and its exciton-coupled circular dichroism

Bioorg Med Chem. 2010 Jan 15;18(2):567-72. doi: 10.1016/j.bmc.2009.12.009. Epub 2009 Dec 11.

Authors

Yoshiaki Masaki¹, Akihiro Ohkubo, Kohji Seio, Mitsuo Sekine

Affiliation

¹ Department of Life Science, Tokyo Institute of Technology, 4259 Nagatsuta, Midori-ku, Yokohama 226-8501, Japan.

PMID: 20036130
DOI: 10.1016/j.bmc.2009.12.009

Abstract

6-N-(Benzothiazol-2-yl)deoxyadenosine (A(BT)) was synthesized and incorporated into DNAs. Although, the multipoint benzothiazole (BT) modification of oligodeoxynucleotides reduced the stability of duplexes with their complementary strands, it induced the strong exciton coupling between BT moieties. The circular dichroism (CD) spectra of this exciton coupling interaction were observed at wavelengths above 300nm and overlapping with the UV absorption bands of nucleotides could be avoided. The shapes of the CD spectra due to this interaction were strongly influenced by the helicity of two BT groups.

Publication types

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

MeSH terms

Base Sequence
Circular Dichroism
DNA / chemistry
Deoxyadenosines / chemical synthesis*
Deoxyadenosines / chemistry*

Substances

6-N-(benzothiazol-2-yl)deoxyadenosine
Deoxyadenosines
DNA