title: Model compounds for (6-4) photolyases: a comparative flavin induced cleavage study of oxetanes and thietanes.
abstract: 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.
authors.affiliation: Department of Chemistry, Ludwig-Maximilians-University Munich, Butenandtstr. 5-13, 81377, Munich, Germany.
authors.forename: Marcus G
authors.initials: MG
authors.lastname: Friedel
authors.forename: Michaela K
authors.initials: MK
authors.lastname: Cichon
authors.forename: Thomas
authors.initials: T
authors.lastname: Carell
mesh_terms: D002851:Chromatography, High Pressure Liquid; D004988:Ethers, Cyclic / Q000737:chemistry*; D006868:Hydrolysis; D009682:Magnetic Resonance Spectroscopy; D021241:Spectrometry, Mass, Electrospray Ionization
chemical_list: D004988:Ethers, Cyclic; C005287:oxetane