Synthesis of DNA fragments containing 5,6-dihydrothymine, a major product of thymine gamma radiolysis

1 January 1988

journal article
research article
Published by Oxford University Press (OUP) in Nucleic Acids Research

Vol. 16 (1) , 319-326
https://doi.org/10.1093/nar/16.1.319

Abstract

5,6-Dihydrothymine is one of the most important products of base damage by gamma irradiation of DNA in anoxic conditions. This modified base is unstable in the deprotection conditions used for classical synthesis of oligonucleotides. For its incorporation in synthetic DNA fragments, a new set of amino protecting groups has been developed. The 5,6-dihydrothymidine phosphoramidite was successfully employed for the synthesis of two 14-mers and one 17-mer bearing this defect at positions corresponding to restriction enzymes sites. The presence of the modified base still intact in the oligonucleotides was evidenced by mass spectrometry in pyrolytic conditions.

This publication has 16 references indexed in Scilit:

[57] Sequencing end-labeled DNA with base-specific chemical cleavages
Published by Elsevier ,2004
Palindromic octa- and dodecanucleotides containing 2'-deoxytubercidin: synthesis, hairpin formation, and recognition by the endodeoxyribonuclease EcoRI
Biochemistry, 1987
Synthesis of decadeoxyribonucleotides containing N⁶-methyladenine, N⁴-methylcytosine, and 5-methylcytosine: recognition and cleavage by restriction endonucleases (nucleosides and nucleotides part 74)¹
Nucleic Acids Research, 1987
The final deprotection step in oligonucleotide synthesis is reduced to a mild and rapid ammonia treatment by using labile base-protecting groups
Nucleic Acids Research, 1987
Hybridization triggered cross-linking of deoxyoligonucleotides
Nucleic Acids Research, 1986
Polymer support oligonucleotide synthesis XVIII^1.2): use ofβ-cyanoethyi-N,N-dialkylamino-/N-morpholino phosphoramidite of deoxynucleosides for the synthesis of DNA fragments simplifying deprotection and isolation of the final product
Nucleic Acids Research, 1984
Syringe method for stepwise chemical synthesis of oligonucleotides
Nucleic Acids Research, 1982
New effective method for the synthesis of oligonucleotides via phosphotriester intermediates
Nucleic Acids Research, 1982
Detection and identification of minor nucleotides in intact deoxyribonucleic acids by mass spectrometry
Nucleic Acids Research, 1976
[Acid and enzyme hydrolysis of the thymine fragment modified and bound to the polynucleotide chain after in vitro gamma irradiation of DNA of E. coli].
1974