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 |
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Keywords
- Streptomyces hygroscopicus
- Tricyclic geldanamycin analogues
ASJC Scopus subject areas
- Biochemistry
- Organic Chemistry
- Drug Discovery
Cite this
New tricyclic geldanamycin analogues from an engineered strain of Streptomyces hygroscopicus JCM4427. / Hong, Seong Su; Cai, Xing Fu; Hwang, Bang Yeon; Lee, Hong Sub; Su, Bao Ning; Hong, Young Soo; Lee, Dongho.
In: Tetrahedron Letters, Vol. 51, No. 2, 13.01.2010, p. 351-353.Research output: Contribution to journal › Article
}
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 -