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

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 (ΔtamI) 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.

Citation

Xingwang Zhang, Zhong Li, Lei Du, George E Chlipala, Patricia C Lopez, Wei Zhang, David H Sherman, Shengying Li. Identification of an unexpected shunt pathway product provides new insights into tirandamycin biosynthesis. Tetrahedron letters. 2016 Dec 28;57(52):5919-5923

PMID: 28989201

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