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萘霉素,由链霉菌属KB - 3346 - 5产生的耐甲氧西林金黄色葡萄球菌中β-内酰胺抗性的新型规避剂。II. 结构解析。

Naphthacemycins, novel circumventors of β-lactam resistance in MRSA, produced by Streptomyces sp. KB-3346-5. II. Structure elucidation.

作者信息

Fukumoto Atsushi, Kim Yong-Pil, Iwatsuki Masato, Hirose Tomoyasu, Sunazuka Toshiaki, Hanaki Hideaki, Ōmura Satoshi, Shiomi Kazuro

机构信息

Graduate School of Infection Control Sciences, Kitasato University, Tokyo, Japan.

Kitasato Institute for Life Sciences, Kitasato University, Tokyo, Japan.

出版信息

J Antibiot (Tokyo). 2017 May;70(5):568-573. doi: 10.1038/ja.2017.29. Epub 2017 Mar 15.

Abstract

Seventeen new compounds, naphthacemycins A-A, B-B and C-C, were isolated from a cultured broth of Streptomyces sp. KB-3346-5 during screening for circumventors of β-lactam resistance in methicillin-resistant Staphylococcus aureus. Their structures were elucidated by spectroscopic studies, including NMR and X-ray crystallographic analysis. The naphthacemycin A series has a new skeleton displaying a 7-phenylnaphthacene-5,6,11(12H)-trione. In contrast, the quinone moiety of the A series is changed to dehydroxyquinol in the B series and to a semiquinone-like structure in the C series.

摘要

在筛选耐甲氧西林金黄色葡萄球菌中β-内酰胺耐药规避剂的过程中,从链霉菌属KB-3346-5的培养肉汤中分离出17种新化合物,即萘并霉素A-A、B-B和C-C。通过包括核磁共振(NMR)和X射线晶体学分析在内的光谱研究确定了它们的结构。萘并霉素A系列具有一个新骨架,呈现7-苯基萘并[2,3-b]蒽-5,6,11(12H)-三酮。相比之下,A系列的醌部分在B系列中变为脱羟基醌醇,在C系列中变为类似半醌的结构。

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