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

Seong Su Hong; Xing Fu Cai; Bang Yeon Hwang; Hong Sub Lee; Bao Ning Su; Young Soo Hong; Dongho Lee

doi:10.1016/j.tetlet.2009.11.018

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

Seong Su Hong, Xing Fu Cai, Bang Yeon Hwang, Hong Sub Lee, Bao Ning Su, Young Soo Hong, Dongho Lee

Department of Biosystems and Biotechnology

Research output: Contribution to journal › Article › peer-review

2 Citations (Scopus)

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	https://doi.org/10.1016/j.tetlet.2009.11.018
Publication status	Published - 2010 Jan 13

Keywords

Streptomyces hygroscopicus
Tricyclic geldanamycin analogues

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2009.11.018

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@article{aa6f331fddf541ae84a0fcc95aa19e51,

title = "New tricyclic geldanamycin analogues from an engineered strain of Streptomyces hygroscopicus JCM4427",

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",

author = "Hong, {Seong Su} and Cai, {Xing Fu} and Hwang, {Bang Yeon} and Lee, {Hong Sub} and Su, {Bao Ning} and Hong, {Young Soo} and Dongho Lee",

note = "Funding Information: This work was supported by the 21C Frontier Microbial Genomics and Application Center, the Ministry of Education, Science and Technology, Republic of Korea and by a grant from KRIBB Research Initiative Program. We thank Cooperative Center for Analytical Instruments at Korea University for providing some of the equipment used in this study. ",

year = "2010",

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doi = "10.1016/j.tetlet.2009.11.018",

language = "English",

volume = "51",

pages = "351--353",

journal = "Tetrahedron Letters",

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T1 - New tricyclic geldanamycin analogues from an engineered strain of Streptomyces hygroscopicus JCM4427

AU - Hong, Seong Su

AU - Cai, Xing Fu

AU - Hwang, Bang Yeon

AU - Lee, Hong Sub

AU - Su, Bao Ning

AU - Hong, Young Soo

AU - Lee, Dongho

N1 - Funding Information: This work was supported by the 21C Frontier Microbial Genomics and Application Center, the Ministry of Education, Science and Technology, Republic of Korea and by a grant from KRIBB Research Initiative Program. We thank Cooperative Center for Analytical Instruments at Korea University for providing some of the equipment used in this study.

PY - 2010/1/13

Y1 - 2010/1/13

N2 - 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).

AB - 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).

KW - Streptomyces hygroscopicus

KW - Tricyclic geldanamycin analogues

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DO - 10.1016/j.tetlet.2009.11.018

M3 - Article

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VL - 51

SP - 351

EP - 353

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 2

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

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