New tricyclic geldanamycin analogues from an engineered strain of Streptomyces hygroscopicus JCM4427

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Title
New tricyclic geldanamycin analogues from an engineered strain of Streptomyces hygroscopicus JCM4427
Author(s)
S S Hong; X F Cai; B Y Hwang; H S Lee; B N Su; Young-Soo Hong; D Lee
Bibliographic Citation
Tetrahedron Letters, vol. 51, no. 2, pp. 351-353
Publication Year
2010
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).
Keyword
Streptomyces hygroscopicusTricyclic geldanamycin analogues
ISSN
0040-4039
Publisher
Elsevier
DOI
http://dx.doi.org/10.1016/j.tetlet.2009.11.018
Type
Article
Appears in Collections:
Ochang Branch Institute > Chemical Biology Research Center > 1. Journal Articles
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