Vertirhodins A-F, C-Linked Pyrrolidine-Iminosugar-Containing Pyranonaphthoquinones from Streptomyces sp. B15-008.

Vertirhodins A-F, C-Linked Pyrrolidine-Iminosugar-Containing Pyranonaphthoquinones from Streptomyces sp. B15-008.
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DOI:
10.1021/acs.orglett.0c03825
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发表时间:
2021-02-05
期刊:
影响因子:
5.2
通讯作者:
Bewley, Carole A.
Bewley, Carole A.
中科院分区:
化学1区
文献类型:
--
作者:
Sun, Jiadong;Zhao, Gengxiang;OConnor, Robert D.;Davison, Jack R.;Bewley, Carole A.

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从土壤来源的链霉菌B15 - 008中发现了6个新的吡喃萘醌类化合物,分别命名为vertirhodins A-F(1 - 6)。利用核磁共振以及实验和理论电子圆二色性光谱的比较确定了它们的化学结构和绝对构型。vertirhodins具有不寻常的C-8 N-甲基-2-吡咯烷甲醇部分,在链霉菌衍生的天然产物中很少见到的5,14-环氧化物,以及形成半醌的C-13羟基。通过全基因组测序确定了一个合理的ver生物合成基因簇,并提供了对这些特征的见解。
Six novel pyranonaphthoquinones, vertirhodins A–F (1–6), were discovered from a soil-derived Streptomyces sp. B15–008. Their chemical structures and absolute configurations were determined using nuclear magnetic resonance and comparison of experimental and theoretical electronic circular dichroism spectra. The vertirhodins feature an unusual C-8 N-methyl-2-pyrrolidinemethanol moiety, a 5,14-epoxide rarely seen in streptomyces-derived natural products, and a C-13 hydroxyl group that forms the semiquinone. A plausible ver biosynthetic gene cluster was identified through whole genome sequencing and provides insights into these features.
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