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Nucleic Acids Res. May 25, 1991; 19(10): 2587–2593.
PMCID: PMC328174

Influence of the incorporation of (S)-9-(3,4-dihydroxybutyl)adenine on the enzymatic stability and base-pairing properties of oligodeoxynucleotides.

Abstract

(S)-9-(3,4-dihydroxybutyl)adenine was used at several positions as nucleoside substitute in the synthesis of dimers and 13-mers. Therefore we used the phosporamidite and the H-phosphonate chemistry. The nuclease susceptibilities and the base-pairing properties of these oligomers have been evaluated.

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  • Hayashi H, Nakanishi K, Brandon C, Marmur J. Structure and synthesis of dihydroxypentyluracil from bacteriophage SP-15 deoxyribonucleic acid. J Am Chem Soc. 1973 Dec 26;95(26):8749–8757. [PubMed]
  • Froehler BC, Ng PG, Matteucci MD. Synthesis of DNA via deoxynucleoside H-phosphonate intermediates. Nucleic Acids Res. 1986 Jul 11;14(13):5399–5407. [PMC free article] [PubMed]
  • Pon RT, Usman N, Ogilvie KK. Derivatization of controlled pore glass beads for solid phase oligonucleotide synthesis. Biotechniques. 1988 Sep;6(8):768–775. [PubMed]
  • Weinfeld M, Liuzzi M, Paterson MC. Selective hydrolysis by exo- and endonucleases of phosphodiester bonds adjacent to an apurinic site. Nucleic Acids Res. 1989 May 25;17(10):3735–3745. [PMC free article] [PubMed]
  • Stein CA, Subasinghe C, Shinozuka K, Cohen JS. Physicochemical properties of phosphorothioate oligodeoxynucleotides. Nucleic Acids Res. 1988 Apr 25;16(8):3209–3221. [PMC free article] [PubMed]

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