Dioxygenase-catalysed oxidation of monosubstituted thiophenes: sulfoxidation versus dihydrodiol formation

…, N Gunaratne, SA Haughey, MA Kennedy…

Index: Boyd, Derek R; Sharma, Narain D; Gunaratne, Nimal; Haughey, Simon A; Kennedy, Martina A; Malone, John F; Allen, Christopher C; Dalton, Howard Organic and biomolecular chemistry, 2003 , vol. 1, # 6 p. 984 - 994

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Citation Number: 25

Abstract

Toluene dioxygenase (TDO)-catalysed sulfoxidation, using Pseudomonas putida UV4, was observed for the thiophene substrates 1A–1N. The unstable thiophene oxide metabolites, 6A–6G, 6K–6N, spontaneously dimerised yielding the corresponding racemic disulfoxide cycloadducts 7A–7G, 7K–7N. Dimeric or crossed [4+ 2] cycloaddition products, derived from the thiophene oxide intermediates 6A and 6D or 6B and 6D, were found when mixtures of ...