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.
Friedel
Marcus G
MG
Department of Chemistry, Ludwig-Maximilians-University Munich, Butenandtstr. 5-13, 81377, Munich, Germany.
Cichon
Michaela K
MK
Carell
Thomas
T
D002851:Chromatography, High Pressure Liquid; D004988:Ethers, Cyclic / Q000737:chemistry*; D006868:Hydrolysis; D009682:Magnetic Resonance Spectroscopy; D021241:Spectrometry, Mass, Electrospray Ionization
D004988:Ethers, Cyclic; C005287:oxetane