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Chemical ligation and recombination of DNA fragments through formation (exchange) of disulfide bonds located in the sugar-phosphate backbone

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Abstract

Effective methods of the directed introduction of diphosphoryl disulfide bridges into hairpin DNA duplexes in place of natural phosphodiester groups were developed using the H2O2-effected ligation of 3′- and 5′-thiophosphorylated oligonucleotides or by autoligation of a preactivated oligonucleotide derivative with a phosphorothioate-bearing oligomer. The postsynthetic recombination of the disulfide-linked oligonucleotide fragments was characterized. It was shown that, along with template-directed reactions, out-of-duplex formation and exchange of diphosphoryl disulfide bonds in the DNA sugar-phosphate backbone may occur. In modified hairpin DNA, a spontaneous exchange of disulfide-linked fragments virtually does not take place because of the intramolecular duplex formation.

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Abbreviations

EDC:

1-ethyl-3-(3-dimethylaminopropyl)carbodi-imide hydrochloride

Sp(i) or (i)pS:

5′- or 3′-thiophosphoryl oligonucleotide (i)

(i)pSSp(j) (heterodimer):

oligonucleotides (i) and (j) linked through a (3′-5′)diphosphoryl disulfide bridge

(i)pSSp(i) (homodimer):

bis[oligonucleotide (i)]-(3′-3′)- or (5′-5′)diphosphoryl disulfide

MES:

morpholinoethanesulfonic acid

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Authors and Affiliations

  1. Chemical Faculty, Moscow State University, Vorob’evy gory, 119899, GSP-3 Moscow, Russia

    N. G. Dolinnaya & V. G. Metelev

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  1. N. G. Dolinnaya
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  2. V. G. Metelev
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Correspondence to N. G. Dolinnaya.

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Dolinnaya, N.G., Metelev, V.G. Chemical ligation and recombination of DNA fragments through formation (exchange) of disulfide bonds located in the sugar-phosphate backbone. Russ J Bioorg Chem 26, 277–284 (2000). https://doi.org/10.1007/BF02759167

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  • DOI: https://doi.org/10.1007/BF02759167

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