Evidence that the (6-4) photolyase mechanism can proceed through an oxetane intermediate.

Saâdia Asgatay, Christian Petermann, Dominique Harakat, Dominique Guillaume, John-Stephen Taylor, Pascale Clivio

Journal: Journal of the American Chemical Society 2008;130(38):12618-9

PMID: 18763765

Full Text on American Chemical Society View on PubMed

Abstract

Using the analogue of TpT methylated at the 3'-end N3 position (Tpm3T), we demonstrate that when the oxetane/(6-4) pathway is precluded, water addition occurs at the 3'-end C6 position of the oxetane intermediate to provide its opening. Photoreversal of this (6-4) photoproduct C6 hydrate brings the first experimental evidence that the (6-4) photolyase repair can proceed through an oxetane intermediate.

Address: Université de Reims Champagne Ardenne, Institut de Chimie Moléculaire de Reims, CNRS UMR 6229, UFR de Pharmacie, 51 rue Cognacq-Jay, 51096 Reims Cedex, France.

DOI: 10.1021/ja805214s

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MeSH Terms: DNA, Deoxyribodipyrimidine Photo-Lyase, Ethers, Cyclic, Glycosides, Imines, Photochemistry, Pyrimidine Dimers