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

Access to Document

10.1016/j.tetlet.2009.11.018

Fingerprint Dive into the research topics of 'New tricyclic geldanamycin analogues from an engineered strain of Streptomyces hygroscopicus JCM4427'. Together they form a unique fingerprint.

Cite this

@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",

year = "2010",

month = jan,

day = "13",

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

language = "English",

volume = "51",

pages = "351--353",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "2",

}

TY - JOUR

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

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

UR - http://www.scopus.com/inward/record.url?scp=71049171242&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=71049171242&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2009.11.018

DO - 10.1016/j.tetlet.2009.11.018

M3 - Article

AN - SCOPUS:71049171242

VL - 51

SP - 351

EP - 353

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 2

ER -