Application of base-catalysed reaction to the synthesis of dinucleotides containing the four common deoxyribonucleosides and of oligodeoxythymidylates | Zendy

Richard von Tigerstrom | Zendy; Patricia Jahnke | Zendy; Vivian Wylie | Zendy; Michael J. Smith | Zendy

Open Access

Application of base-catalysed reaction to the synthesis of dinucleotides containing the four common deoxyribonucleosides and of oligodeoxythymidylates

Author(s) -

Richard von Tigerstrom,

Patricia Jahnke,

Vivian Wylie,

Michael J. Smith

Publication year - 1975

Publication title -

nucleic acids research

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 9.008

H-Index - 537

eISSN - 1362-4954

pISSN - 0305-1048

DOI - 10.1093/nar/2.10.1737

Subject(s) - deoxyribonucleosides , pyrimidine , purine , yield (engineering) , deoxyribonucleoside , biology , nucleotide , dna , nucleoside , depurination , purine metabolism , potassium , nucleic acid , stereochemistry , biochemistry , chemistry , organic chemistry , materials science , gene , metallurgy , enzyme

The phosphorylation of nucleosides by a nucleoside phosphorofluoridate in the presence of potassium tert-butoxide is a very effective reaction for internucleotide bond synthesis in the case of pyrimidine deoxynucleosides. However, for the purine deoxynucleosides, yields are reduced due to competing reactions. The method was applied to the stepwise synthesis of oligothymidylates. The yield of the trinucleotide was good whereas that of the tetranucleotide was reduced due to the insolubility of the intermediate trinucleotide in the presence of potassium tert-butoxide.

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