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Issue 10, 2005
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Model compounds for (6–4) photolyases: a comparative flavin induced cleavage study of oxetanes and thietanes

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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.

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

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Supplementary files

Article information


Submitted
04 Mar 2005
Accepted
24 Mar 2005
First published
18 Apr 2005

Org. Biomol. Chem., 2005,3, 1937-1941
Article type
Paper

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

M. G. Friedel, M. K. Cichon and T. Carell, Org. Biomol. Chem., 2005, 3, 1937
DOI: 10.1039/B503205A

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