Identification of an unexpected shunt pathway product provides new insights into tirandamycin biosynthesis

TETRAHEDRON LETTERS

卷:57

Article

Zhang, Xingwang^1,2  Li, Zhong^1,2,3  Du, Lei^1,2,3  Chlipala, George E.^4,5,6  Lopez, Patricia C.^4,5,6  Zhang, Wei^1,2  Sherman, David H.^4,5,6  Li, Shengying^1,2 

[1] Chinese Acad Sci, Shandong Prov Key Lab Synthet Biol, Qingdao Inst Bioenergy & Bioproc Technol, Qingdao 266101, Shandong, Peoples R China

[2] Chinese Acad Sci, Qingdao Inst Bioenergy & Bioproc Technol, CAS Key Lab Biofuels, Qingdao 266101, Shandong, Peoples R China

[3] Univ Chinese Acad Sci, Beijing 100049, Peoples R China

[4] Univ Michigan, Inst Life Sci, Dept Med Chem, Ann Arbor, MI 48109 USA

[5] Univ Michigan, Inst Life Sci, Dept Chem, Ann Arbor, MI 48109 USA

[6] Univ Michigan, Inst Life Sci, Dept Microbiol & Immunol, Ann Arbor, MI 48109 USA

关键词: Tirandamycin;    Natural product;    Tetramic acid;    Biosynthesis;    Streptomyces;   

DOI  :  10.1016/j.tetlet.2016.11.080

来源: Elsevier

【 摘 要 】

Tirandamycin K (7), the first linear 7,13;9,13-diseco-tirandamycin derivative, was isolated from the tamI (encoding the TamI P450 monooxygenase) disruption mutant strain (Delta tamI) of marine Streptomyces sp. 307-9. Its chemical structure with relative and absolute configurations was elucidated by a combination of extensive spectroscopic analyses and biosynthetic inferences. Structural elucidation of this unusual compound provides new insights into tirandamycin biosynthesis. Moreover, examination of the biological activity of 7 confirms the essential function of the bicyclic ketal ring for antibiotic activities of tirandamycins. (C) 2016 Published by Elsevier Ltd.

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