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).
| Original language | English |
|---|---|
| Pages (from-to) | 351-353 |
| Number of pages | 3 |
| Journal | Tetrahedron Letters |
| Volume | 51 |
| Issue number | 2 |
| DOIs | |
| Publication status | Published - 2010 Jan 13 |
Keywords
- Streptomyces hygroscopicus
- Tricyclic geldanamycin analogues
ASJC Scopus subject areas
- Biochemistry
- Organic Chemistry
- Drug Discovery
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Cite this
Hong, S. S., Cai, X. F., Hwang, B. Y., Lee, H. S., Su, B. N., Hong, Y. S., & Lee, D. (2010). New tricyclic geldanamycin analogues from an engineered strain of Streptomyces hygroscopicus JCM4427. Tetrahedron Letters, 51(2), 351-353. https://doi.org/10.1016/j.tetlet.2009.11.018