It is now established that the formation of C-S bonds during the conversion
of dethiobiotin into biotin involves intermediate carbon radicals. To exam
ine the behavior of dethiobiotin analogs that could lead to allylic and alp
ha-epoxyradicals, we have synthesized 4,5-dehydrodethiobiotins and the corr
esponding epoxides and 5,6-dehydrodethiobiotins. All these compounds have b
een labelled with C-14 On the carboxyl group. (C) 1999 Elsevier Science Ltd
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