马杜拉他汀 D1 和 D2，一种从. 中分离出的含有恶唑啉的铁载体
Madurastatin D1 and D2, Oxazoline Containing Siderophores Isolated from an .
机构信息
Pharmaceutical Sciences Division , University of Wisconsin-Madison , 777 Highland Avenue , Madison , Wisconsin 53705 , United States.
Department of Genetics , University of Wisconsin-Madison , 425 G Henry Mall , Madison , Wisconsin 53706 , United States.
出版信息
Org Lett. 2019 Aug 16;21(16):6275-6279. doi: 10.1021/acs.orglett.9b02159. Epub 2019 Aug 5.
Abstract
Two new siderophores, madurastatin D1 and D2, together with (-)-madurastatin C1, the enantiomer of a known compound, were isolated from marine-derived sp. The presence of an unusual 4-imidazolidinone ring in madurastatins D1 and D2 inspired us to sequence the sp. genome and to identify the biosynthetic gene cluster, knowledge of which enables us to now propose a biosynthetic pathway. Madurastatin D1 and D2 are moderately active in antimicrobial assays with .
摘要
从海洋来源的 sp. 中分离得到了两种新的铁载体，马杜拉他汀 D1 和 D2，以及（-）-马杜拉他汀 C1，这是一种已知化合物的对映体。马杜拉他汀 D1 和 D2 中存在一个不寻常的 4-咪唑烷酮环，这启发我们对 sp. 的基因组进行测序，并鉴定其生物合成基因簇，这些知识使我们现在能够提出一种生物合成途径。马杜拉他汀 D1 和 D2 在抗微生物测定中对 具有中等活性。
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3
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4
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J Nat Prod. 2017 Jan 27;80(1):2-11. doi: 10.1021/acs.jnatprod.6b00948. Epub 2016 Dec 28.
6
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8
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9
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J Antibiot (Tokyo). 2014 Aug;67(8):577-80. doi: 10.1038/ja.2014.19. Epub 2014 Mar 12.
10
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Mar Drugs. 2013 Dec 16;11(12):5089-99. doi: 10.3390/md11125089.
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