Model compounds for (6-4) photolyases: a comparative flavin induced cleavage study of oxetanes and thietanes

Thietanes were used in the past as mimics for an unstable oxetane intermediate formed during the repair of mutagenic (6-4) lesions. The thietane derivatives were found to be not repaired, raising the question of how well thietanes are cleaved by single electron donation compared to oxetanes. We have prepared two flavin-containing oxetane and thietane model compounds for the (6-4) photolyase catalyzed repair process and we show that both are efficiently cleaved by a reduced and deprotonated flavin. Thietanes are therefore excellent models. The lack of their repair can be attributed to lack of binding.