Synthesis and base pairing studies of geranylated 2-thiothymidine, a natural variant of thymidine

Rui Wang; Srivathsan V Ranganathan; Maria Basanta-Sanchez; Fusheng Shen; Alan Chen; Jia Sheng

doi:10.1039/c5cc07479g

Synthesis and base pairing studies of geranylated 2-thiothymidine, a natural variant of thymidine

Chem Commun (Camb). 2015 Nov 25;51(91):16369-72. doi: 10.1039/c5cc07479g.

Authors

Rui Wang¹, Srivathsan V Ranganathan², Maria Basanta-Sanchez², Fusheng Shen¹, Alan Chen¹, Jia Sheng¹

Affiliations

¹ Department of Chemistry, University at Albany, State University of New York, 1400 Washington Ave. Albany, NY 12222, USA. [email protected] and The RNA Institute, University at Albany, State University of New York, 1400 Washington Ave. Albany, NY 12222, USA.
² The RNA Institute, University at Albany, State University of New York, 1400 Washington Ave. Albany, NY 12222, USA.

PMID: 26405057
DOI: 10.1039/c5cc07479g

Abstract

The synthesis and base pairing of DNA duplexes containing the geranylated 2-thiothymidine have been investigated. This naturally existing hydrophobic modification could grant better base pairing stability to the T-G pair over normal T-A and other mismatched pairs in the duplex context. This study provides a potential explanation for the different codon recognition preferences of the geranylated tRNAs.

Publication types

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

MeSH terms

Base Pairing*
Base Sequence
Molecular Dynamics Simulation
Nucleic Acid Denaturation
Oligodeoxyribonucleotides / chemical synthesis
Oligodeoxyribonucleotides / chemistry*
Terpenes / chemical synthesis*
Thymidine / analogs & derivatives*
Thymidine / chemical synthesis*

Substances

Oligodeoxyribonucleotides
Terpenes
Thymidine