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


ABSTRACT: 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 (?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.

SUBMITTER: Zhang X 

PROVIDER: S-EPMC5628624 | biostudies-literature | 2016 Dec

REPOSITORIES: biostudies-literature

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

Zhang Xingwang X   Li Zhong Z   Du Lei L   Chlipala George E GE   Lopez Patricia C PC   Zhang Wei W   Sherman David H DH   Li Shengying S  

Tetrahedron letters 20161119 52


Tirandamycin K (<b>7</b>), the first linear 7,13;9,13-diseco-tirandamycin derivative, was isolated from the <i>tamI</i> (encoding the TamI P450 monooxygenase) disruption mutant strain (<i>ΔtamI</i>) of marine <i>Streptomyces</i> 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 biosynthes  ...[more]

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