Synthesis of new deazaflavins with planar chirality. Redox-induced "rope-skipping" racemization

Seiji Shinkai, Toshiro Yamaguchi, Hideki Nakao, Osamu Manabe

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13 Citations (Scopus)


New 5-deazaflavins with planar chirality (dFl(n)) were synthesized in which N(3) and O(2′α) in the 10-(2′-hydroxy)phenyl group were linked by a {A figure is presented} chain (n=8,10). (+)-dFl(n=8) showed a large chiral discrimination in fluorescence quenching by (R)- and (S)-1,1′-bi-2- naphthol. (+)-dFl(n=10), which was optically stable at ambient conditions, racemized only when it was converted to the reduced form. This is the first example for redox-induced rope-skipping racemization.

Original languageEnglish
Pages (from-to)1611-1614
Number of pages4
JournalTetrahedron Letters
Issue number14
Publication statusPublished - 1986
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry


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