47 Dynemicin A及び関連化合物の生合成と活性(口頭発表の部)

概要

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Biosynthetic studies of dynemicin A (DNM-A) were carried out on the basis of the incorporation of singly and doubly ^<13>C-labeled acetates, Imethyl-^<13>CImethionine and I^<15>N, 2-^<13>CIglycine by cultures of Micromonospora chersina N956-1. The incorporation results show that the compound is bio-synthesized from two heptaketide chains to compose the bicyclic enediyne core and the anthraquinone moiety, respectively, both of which are derived from seven head to tail coupled acetate units, the carboxyl group derived from one carbon of an acetate unit and the O-methyl group derived from methionine. Intact incorporation of glycine was not observed but a carbon was incorporated into the O-methyl group. The related C_<15> enediyne ring skeleton in the esperamicin/calicheamicin class of antibiotics may be similarly derived as the enediyne core of DNM-A. DNM-A rearranged smoothly to dynemicin H, on treatment with aqueous sodium hydrosulfite in dioxane. The same reaction in d_8-dioxane gave DNM-H deuterated specifically at 24- and 27-positions indicating the generation of biradical species at these positions. Dynemicins O, P and Q which have a bridging phenylene group, a vicinal diol and an oxo group in place of the respective 1,5-diyn-3-ene bridge, the epoxide and the carboxyl group in DNM-A. They also showed rather high activities against bacteria and tumor cells.
天然有機化合物討論会の論文
1991-09-07