Enantiodifferentiating Z-E photoisomerization of cyclooctene sensitized by DNA and RNA.

N. Sugahara, M. Kawano, T. Wada, Y. Inoue

Research output: Contribution to journalArticlepeer-review

12 Citations (Scopus)

Abstract

DNA and RNA have been shown for the first time to function as chiral photosensitizers in aqueous solution, to effect the enantiodifferentiating photoisomerization of (Z)-cyclooctene (1Z), giving the chiral (E)-isomer in enantiomeric excesses (ee's) of up to 15%. In order to elucidate the effect of nucleotide sequence, enantiodifferentiating photoisomerization of 1Z was also performed using oligo and homopolynucleotides as chiral sensitizer. The -18.8% ee was observed by using d(T)15.d(A)15 as sensitizer, whereas sensitization by the poly(U).poly(A) duplex gave only racemic (E)-cyclooctene. From these results, oligothymidine sequence is essential for efficient enantioselective photoisomerization of 1Z.

Original languageEnglish
Pages (from-to)115-116
Number of pages2
JournalNucleic acids symposium series
Issue number44
DOIs
Publication statusPublished - 2000
Externally publishedYes

ASJC Scopus subject areas

  • Medicine(all)

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