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

Authors
Hong, Seong SuCai, Xing FuHwang, Bang YeonLee, Hong SubSu, Bao-NingHong, Young-SooLee, Dongho
Issue Date
13-1월-2010
Publisher
PERGAMON-ELSEVIER SCIENCE LTD
Keywords
Streptomyces hygroscopicus; Tricyclic geldanamycin analogues
Citation
TETRAHEDRON LETTERS, v.51, no.2, pp.351 - 353
Indexed
SCIE
SCOPUS
Journal Title
TETRAHEDRON LETTERS
Volume
51
Number
2
Start Page
351
End Page
353
URI
https://scholar.korea.ac.kr/handle/2021.sw.korea/117164
DOI
10.1016/j.tetlet.2009.11.018
ISSN
0040-4039
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). (C) 2009 Elsevier Ltd. All rights reserved.
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