5-Mercuricytosine: An Organometallic Janus Nucleobase

Dattatraya Ukale; Vaishali S Shinde; Tuomas Lönnberg

doi:10.1002/chem.201600851

5-Mercuricytosine: An Organometallic Janus Nucleobase

Chemistry. 2016 Jun 1;22(23):7917-23. doi: 10.1002/chem.201600851. Epub 2016 Apr 26.

Authors

Dattatraya Ukale^{1

2}, Vaishali S Shinde², Tuomas Lönnberg³

Affiliations

¹ Department of Chemistry, University of Turku, Vatselankatu 2, 20014, Turku, Finland.
² Department of Chemistry, Savirtibai Phule Pune University, Pune, 411007, India.
³ Department of Chemistry, University of Turku, Vatselankatu 2, 20014, Turku, Finland. tuanlo@utu.fi.

PMID: 27113075
DOI: 10.1002/chem.201600851

Abstract

The base-pairing properties of 5-mercuricytosine have been explored at the monomer level by NMR titrations and at the oligonucleotide level by melting temperature measurements. The NMR studies revealed a relatively high affinity for guanine, hypoxanthine, and uridine, that is, bases that are deprotonated upon coordination of Hg(II) . Within an oligonucleotide duplex, 5-mercuricytosine formed Hg(II) -mediated base pairs with thymine and guanine. In the former case, the duplex formed was as stable as the respective duplex comprising solely Watson-Crick base pairs. Based on detailed thermodynamic analysis of the melting curves, the stabilization by the Hg(II) -mediated base pairs may be attributed to a comparatively low entropic penalty of hybridization.

Keywords: base pair; hybridization; mercury; oligonucleotides; organometallic.

Publication types

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

MeSH terms

Base Pairing*
Cytosine / analogs & derivatives*
Guanine / chemistry
Mercury / chemistry*
Nucleic Acid Conformation
Nucleic Acid Hybridization
Oligonucleotides / chemistry*
Thermodynamics
Thymine / chemistry

Substances

Oligonucleotides
Guanine
Cytosine
Mercury
Thymine