A new odorless procedure for the synthesis of 2'-deoxy-6-thioguanosine and its incorporation into oligodeoxynucleotides

Kazumitsu Onizuka, Yosuke Taniguchi, Shigeki Sasaki

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

6-S-[2-[(2-ethylhexyl)oxycarbonyl]ethyl)}-3',5'-O-bis(tert- butyldimethylsilyl)-2'-deoxy-6-thiogua nosine (2) was synthesized in high yield from the corresponding 6-O-mesitylenesulfonyl derivative by the reaction with 2-ethylhexyl 3-mercapto-propionate. The phosphoramidite precursor derived from 2 was successfully applied to an automated DNA synthesizer to produce 2'-deoxy-6-thioguanosine containing ODN. The results showed that 2-ethylhexyl 3-mercaptopropionate is useful as an odor less reagent and also as an S-protecting group of 2'-deoxy-6-thioguanosine.

Original languageEnglish
Pages (from-to)752-760
Number of pages9
JournalNucleosides, Nucleotides and Nucleic Acids
Volume28
Issue number8
DOIs
Publication statusPublished - 2009 Aug 1
Externally publishedYes

Keywords

  • 2'-Deoxy-6-thioguanosine
  • 2-Ethylhexyl 3-mercaptopropionate
  • DNA synthesis
  • Odorless synthesis
  • Phosphoroamidite

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Genetics

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