To the top

Page Manager: Webmaster
Last update: 9/11/2012 3:13 PM

Tell a friend about this page
Print version

Synthesis, oligonucleotid… - University of Gothenburg, Sweden Till startsida
To content Read more about how we use cookies on

Contact form


Note! If you want an answer on a question you must specify your email address

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
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


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.

Page Manager: Webmaster|Last update: 9/11/2012

The University of Gothenburg uses cookies to provide you with the best possible user experience. By continuing on this website, you approve of our use of cookies.  What are cookies?