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New tricyclic geldanamycin analogues from an engineered strain of Streptomyces hygroscopicus JCM4427 |
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| Authors: | Seong Su Hong Bang Yeon Hwang Bao-Ning Su Dongho Lee |
| Institution: | a School of Life Sciences and Biotechnology, Korea University, Seoul 136-713, Republic of Korea b Korea Research Institute of Bioscience and Biotechnology, Daejeon 305-806, Republic of Korea c College of Pharmacy, Chungbuk National University, Cheongju, Chungbuk 361-763, Republic of Korea d Ildong Pharmaceutical Co., Ltd, Hwaseong, Gyeonggi 445-170, Republic of Korea e Division of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, The Ohio State University, Columbus, OH 43210, USA |
| Abstract: | Two tricyclic geldanamycin analogues, DHQ5 (1) and DHQ6 (2), were produced by a combinatorial mutant (AC15) contained a site-directed mutagenesis on the geldanamycin polyketide synthase (PKS) gene with inactivation of the post-PKS tailoring genes (gel7) of Streptomyces hygroscopicus JCM4427. The structural diversity of tricyclic geldanamycin analogues is due to the formation of unusual additional rings, which are formed by alkylation of the C-21 position by C-12 in DHQ5 (1) and by electrophilic addition of the C-15 hydroxyl group to the double bond (C-8-C-9), which leads to the migration of the double bond (to C-7-C-8) and the elimination of a carbamoyloxy group in DHQ6 (2). |
| Keywords: | Streptomyces hygroscopicus Tricyclic geldanamycin analogues |
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