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

Research output: Contribution to journalArticlepeer-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 languageEnglish
Pages (from-to)351-353
Number of pages3
JournalTetrahedron Letters
Volume51
Issue number2
DOIs
Publication statusPublished - 2010 Jan 13

Keywords

  • Streptomyces hygroscopicus
  • Tricyclic geldanamycin analogues

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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