Synthesis and optical resolution of a new flavin with axial chirality and redox-dependent racemization

Seiji Shinkai, Hideki Nakao, Osamu Manabe

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

A new flavin (3-methyl-10-(2′-phenyl)phenylisoalloxazine) with restricted rotation about the C(1′)-N(10) single bond was synthesized and optically resoluted for the first time. (+)- Isomer (100% enantiomeric purity) did not racemize at ambient conditions, whereas it racemized invariably when it was reduced (by four different methods). The kinetic studies proved that the novel racemization mode is attributed to conversion of the "planar" oxidized form to the "bent" reduced form.

Original languageEnglish
Pages (from-to)5183-5186
Number of pages4
JournalTetrahedron Letters
Volume26
Issue number42
DOIs
Publication statusPublished - Jan 1 1985
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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