Properties of oligonucleotide with phenyl-substituted carbocyclic nucleoside analogs for the formation of duplex and triplex DNA

Tamer Nasr, Yosuke Taniguchi, Tomoko Takaki, Hidenori Okamura, Shigeki Sasaki

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)

Abstract

(1S,3S,4R)-1-Phenyl-1-thymidyl-3-hydroxy-4-hydroxymethylcyclopentane (10) and their analogs were synthesized, incorporated into the oligodeoxynucleotides, and their properties were evaluated for the formation of duplex and triplex DNA. The known chiral cyclopentanone derivative was converted into the corresponding ketimine sulfonamide derivative, which was subjected to a stereoselective PhLi addition. The formed sulfonamide was hydrolyzed to afford the primary amino group, on which the thymine moiety was built. The benzyl protecting groups were removed to form the nucleoside analog having a phenyl group and the thymine unit at the 1 position of a carbocyclic skeleton (10). In the estimation of the oligodeoxynucleotides incorporating 10 for duplex and triplex formation, the carbocyclic nucleoside analog 10 did not show the stabilizing effect for duplex formation; on the other hand, it stabilized the triplex. Therefore, the skeleton of the phenyl-substituted carbocyclic nucleoside analog 10 may be a platform for the formation of stable triplex DNA.

Original languageEnglish
Pages (from-to)841-860
Number of pages20
JournalNucleosides, Nucleotides and Nucleic Acids
Volume31
Issue number12
DOIs
Publication statusPublished - Dec 1 2012

All Science Journal Classification (ASJC) codes

  • Genetics
  • Biochemistry
  • Molecular Medicine

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