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

Identification of an unexpected shunt pathway product provides new insights into tirandamycin biosynthesis.
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意外分流途径产物的鉴定为替兰霉素生物合成提供了新的见解

DOI:
10.1016/j.tetlet.2016.11.080
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发表时间:
2016-12-28
影响因子:
1.8
通讯作者:
Li S
Li S
中科院分区:
化学4区
文献类型:
--
作者:
Zhang X;Li Z;Du L;Chlipala GE;Lopez PC;Zhang W;Sherman DH;Li S

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从海洋链霉菌307-9的tamI(编码TamI P450单加氧酶)破坏突变株(ΔtamI)中分离得到的第一个线性7,13; 9,13-双辅酶-替兰达霉素衍生物--替兰达霉素K(7)。通过大量的光谱分析和生物合成推断,阐明了其相对构型和绝对构型的化学结构。这种不寻常的化合物的结构解析提供了新的见解替兰达霉素的生物合成。此外,对7的生物活性的检查证实了双环缩酮环对于替兰霉素的抗生素活性的基本功能。
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.
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