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.
All Science Journal Classification (ASJC) codes
- Drug Discovery
- Organic Chemistry