Solution structure of S-DNA formed by covalent base pairing involving a disulfide bond

Akihiko Hatano, Munehiro Okada, Gota Kawai

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Here, we present the solution structure of a DNA duplex containing a disulfide base pair (S-DNA). The unnatural nucleoside "S" possessing a thiophenyl group as base was incorporated into a self-complementary singled-stranded oligonucleotide. Crosslinking of the disulfide base pair was analyzed by non-denaturing polyacrylamide gel electrophoresis. Under oxidizing conditions a high molecular weight band as 18 mer, corresponding to the double-stranded molecule (5′-GCGASTCGC: 3′-CGCTSAGCG), was found, whereas single-stranded self-complementary 9 mer oligonucleotide GCGASTCGC was detected in the presence of a reducing agent. These results suggest that the oligonucleotide is covalently linked by disulfide bonding under oxidizing conditions, which can be reversibly reduced to two thiol groups under reducing conditions. CD spectrum of S-DNA (CGASTCG) under oxidizing conditions suggested that the duplex had a right-handed double-stranded structure similar to that of natural DNA (B-form, CGATCG). NMR studies confirmed that this CGASTCG resembled natural B-DNA and that the two phenyl rings derived from the disulfide base pairing intercalated into the duplex. However, these two phenyl rings were not positioned in the same plane as the other base pairs. Specifically, NOEs suggest that although CGASTCG adopts a structure similar to B-type DNA, the S-DNA duplex is bent at the point of disulfide base pairing to face the major groove.

Original languageEnglish
Pages (from-to)7327-7333
Number of pages7
JournalOrganic and Biomolecular Chemistry
Volume10
Issue number36
DOIs
Publication statusPublished - 2012 Sep 28

Fingerprint

disulfides
Disulfides
deoxyribonucleic acid
DNA
oligonucleotides
Oligonucleotides
B-Form DNA
Reducing Agents
nucleosides
Electrophoresis
Nucleosides
Sulfhydryl Compounds
rings
Crosslinking
crosslinking
electrophoresis
thiols
grooves
Molecular weight
Nuclear magnetic resonance

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Biochemistry

Cite this

Solution structure of S-DNA formed by covalent base pairing involving a disulfide bond. / Hatano, Akihiko; Okada, Munehiro; Kawai, Gota.

In: Organic and Biomolecular Chemistry, Vol. 10, No. 36, 28.09.2012, p. 7327-7333.

Research output: Contribution to journalArticle

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