Micromonosporamide A with Glutamine-Dependent Cytotoxicity from Micromonospora sp. MM609M-173N6: Isolation, Stereochemical Determination, and Synthesis,Organic Letters

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Micromonosporamide A with Glutamine-Dependent Cytotoxicity from Micromonospora sp. MM609M-173N6: Isolation, Stereochemical Determination, and Synthesis
Organic Letters ( IF 4.9 ) Pub Date : 2021-09-29 , DOI: 10.1021/acs.orglett.1c02974
Toshifumi Takeuchi ₁ , Masaki Hatano ₁ , Hideyuki Muramatsu ₁ , Yumiko Kubota ₁ , Ryuichi Sawa ₁ , Masayuki Igarashi ₁

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An acyldipeptide, micromonosporamide A, was isolated from the fermentation broth of Micromonospora sp. MM609M-173N6 by bioassay-guided fractionation using a glutamine compensation assay. The planar structure was elucidated on the basis of comprehensive one- and two-dimensional nuclear magnetic resonance and high-resolution mass spectrometry. The relative and absolute configuration of the entire molecule were determined using a combined approach, involving chromatographic analysis by liquid chromatography–mass spectrometry, advanced Marfey’s method, and total synthesis. Micromonosporamide A exhibited glutamine-dependent antiproliferative activity.

中文翻译：

来自 Micromonospora sp. 的具有谷氨酰胺依赖性细胞毒性的 Micromonosporamide A。MM609M-173N6：分离、立体化学测定和合成

从Micromonospora sp.的发酵液中分离出一种酰基肽，即 micromonosporamide A。MM609M-173N6 通过使用谷氨酰胺补偿测定的生物测定引导分级分离。平面结构是在综合一维和二维核磁共振和高分辨率质谱的基础上阐明的。使用组合方法确定整个分子的相对和绝对构型，包括液相色谱-质谱、高级 Marfey 方法和全合成的色谱分析。Micromonosporamide A 表现出依赖于谷氨酰胺的抗增殖活性。

更新日期：2021-10-15

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