Synthesis and characterisation of oligodeoxynucleotides containing thio analogues of (6-4) pyrimidine-pyrimidinone photo-dimers

Journal of Molecular Biology
M A WarrenB A Connolly

Abstract

A method for the preparation of an oligodeoxynucleotide, 20 bases in length, containing centrally located thio analogues of (6-4) pyrimidine-pyrimidinone thymine photo-dimers is reported. The approach is based on the selective irradiation, at 350 nm, of a Tp4ST (4ST = 4-thiothymidine) step within a 20-mer having the sequence: d(ACTCGGACCT(4sT)CGCTGTGAT). Conversion of the S5-(6-4)/S5-thietane pyrimidine-pyrimidinone, initially formed, to its S5-Dewar isomer is by a subsequent irradiation at 300 nm. Both of the photo-dimer-containing oligonucleotides were purified by HPLC (ion exchange and reverse phase) and characterised by base composition analysis. The S5-(6-4)/S5-thietane pyrimidine-pyrimidinone containing 20-mer has a characteristic UV absorbance at 320 nm and exhibits strong fluorescence when excited at this wavelength. As expected, conversion to the S5-Dewar isomer abolished both the 320 nm absorbance and the fluorescence emission. The lengths of the oligonucleotides produced allowed the formation of stable double-stranded DNA, by hybridisation to a complementary sequence. Examination of these duplexes by circular dichroism spectroscopy showed that they formed B-DNA, with little changes to their gross structure as compare...Continue Reading

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Citations

Aug 17, 2002·Nucleosides, Nucleotides & Nucleic Acids·Galal H Elgemeie, Eman A Kamal
Mar 12, 2004·Bioorganic & Medicinal Chemistry Letters·Yao-Zhong XuPeter Karran
Oct 31, 2003·Organic & Biomolecular Chemistry·Sandra Karina Angulo MatusPascale Clivio
Jan 12, 2019·Physical Chemistry Chemical Physics : PCCP·Bin-Bin Xie, Cheng-Xing Cui
May 26, 2011·British Journal of Cancer·S W PridgeonA V Boddy
Nov 3, 2011·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Olivier ReelfsAntony R Young
Jul 19, 2020·Nature Communications·Luis A Ortiz-RodríguezCarlos E Crespo-Hernández
Sep 25, 2019·Physical Chemistry Chemical Physics : PCCP·Xiaoran ZouChun-Yang Zhang
Jun 8, 2021·Chemical Science·Luis A Ortiz-Rodríguez, Carlos E Crespo-Hernández

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