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Synthesis, oligonucleotide incorporation and fluorescence properties in DNA of a bicyclic thymine analogue

Journal article
Authors Christopher P. Lawson
A. F. Fuchtbauer
M. S. Wranne
T. Giraud
T. Floyd
B. Dumat
N. K. Andersen
A. H. El-Sagheer
T. Brown
H. Graden
L. M. Wilhelmsson
Morten Grötli
Published in Scientific Reports
Volume 8
ISSN 2045-2322
Publication year 2018
Published at Department of Chemistry and Molecular Biology
Language en
Links dx.doi.org/10.1038/s41598-018-31897...
Keywords base analog, nucleic-acids, quadracyclic adenine, circular-dichroism, helix formation, 2-aminopurine, probe, rna, 1,8-naphthyridin-2(1h)-ones, thermodynamics
Subject categories Organic Chemistry

Abstract

Fluorescent base analogues (FBAs) have emerged as a powerful class of molecular reporters of location and environment for nucleic acids. In our overall mission to develop bright and useful FBAs for all natural nucleobases, herein we describe the synthesis and thorough characterization of bicyclic thymidine (bT), both as a monomer and when incorporated into DNA. We have developed a robust synthetic route for the preparation of the bT DNA monomer and the corresponding protected phosphoramidite for solid-phase DNA synthesis. The bT deoxyribonucleoside has a brightness value of 790 M(-1)cm(-1) in water, which is comparable or higher than most fluorescent thymine analogues reported. When incorporated into DNA, bT pairs selectively with adenine without perturbing the B-form structure, keeping the melting thermodynamics of the B-form duplex DNA virtually unchanged. As for most fluorescent base analogues, the emission of bT is reduced inside DNA (4.5- and 13-fold in single- and double-stranded DNA, respectively). Overall, these properties make bT an interesting thymine analogue for studying DNA and an excellent starting point for the development of brighter bT derivatives.

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Denna text är utskriven från följande webbsida:
http://www.gu.se/english/research/publication/?publicationId=271747
Utskriftsdatum: 2019-10-19