麦拉菌素 A-D，一种源自东肯塔基废弃煤矿微生物的格尔德霉素衍生的环戊烯酮大环内酯。
Mccrearamycins A-D, Geldanamycin-Derived Cyclopentenone Macrolactams from an Eastern Kentucky Abandoned Coal Mine Microbe.
机构信息
Center for Pharmaceutical Research and Innovation, College of Pharmacy, University of Kentucky, Lexington, Kentucky, 40536, USA.
Department of Biology, University of Kentucky, Lexington, KY, 40506, USA.
出版信息
Angew Chem Int Ed Engl. 2017 Mar 6;56(11):2994-2998. doi: 10.1002/anie.201612447. Epub 2017 Jan 31.
Abstract
Four cyclopentenone-containing ansamycin polyketides (mccrearamycins A-D), and six new geldanamycins (Gdms B-G, including new linear and mycothiol conjugates), were characterized as metabolites of Streptomyces sp. AD-23-14 isolated from the Rock Creek underground coal mine acid drainage site. Biomimetic chemical conversion studies using both simple synthetic models and Gdm D confirmed that the mccrearamycin cyclopentenone derives from benzilic acid rearrangement of 19-hydroxy Gdm, and thereby provides a new synthetic derivatization strategy and implicates a potential unique biocatalyst in mccrearamycin cyclopentenone formation. In addition to standard Hsp90α binding and cell line cytotoxicity assays, this study also highlights the first assessment of Hsp90α modulators in a new axolotl embryo tail regeneration (ETR) assay as a potential new whole animal assay for Hsp90 modulator discovery.
摘要
从罗克克里克地下煤矿酸性排水点分离到的链霉菌 AD-23-14 中，鉴定出四种含环戊烯酮的安莎霉素聚酮（麦卡雷霉素 A-D）和六种新的金褐霉素（Gdms B-G，包括新的线性和麦硫因缀合物）。使用简单的合成模型和 Gdm D 进行的仿生化学转化研究证实，麦卡雷霉素的环戊烯酮来源于 19-羟基 Gdm 的苯偶姻重排，从而提供了一种新的合成衍生化策略，并暗示了麦卡雷霉素环戊烯酮形成中的一种潜在独特的生物催化剂。除了标准的 Hsp90α 结合和细胞系细胞毒性测定外，本研究还首次在新的蝾螈胚胎尾部再生（ETR）测定中评估了 Hsp90α 调节剂，作为发现 Hsp90 调节剂的潜在新的整体动物测定。
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