Stereostructure of luminamicin, an anaerobic antibiotic, via molecular dynamics, NMR spectroscopy, and the modified Mosher method
Stereostructure of luminamicin, an anaerobic antibiotic, via molecular dynamics, NMR spectroscopy, and the modified Mosher method
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DOI：
10.1073/pnas.0508425102
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发表时间：
2005-12-20
影响因子：
11.1
通讯作者：
Omura, S
中科院分区：
文献类型：
--
作者：
Gouda, H;Sunazuka, T;Omura, S
通过高温分子动力学、核磁共振波谱和改进的Mosher方法进行构象分析，确定了厌氧抗生素鲁米诺霉素的绝对立体结构。发现鲁米诺霉素分别在C2、C4、C7、C9、C10、C11、C12、C13、C16、C28和C29处具有5、S、R、R、R、R、S、S、S、R和S构型。该构型与在阿曲米星中发现的构型相同，阿曲米星的化学结构与鲁米诺霉素非常相似。鲁米诺霉素的结构由三个不同的环组成，即，十氢化萘环、10元大环内酯环和14元大环内酯环。所得到的三维结构的鲁米诺霉素显示出一个有趣的功能，在与14元大环内酯的烯醇醚基团共轭的马来酸酐官能团几乎垂直于其他两个环的平面。
The absolute stereostructure of luminamicin, an anaerobic antibiotic, has been determined by using conformational analysis via high-temperature molecular dynamics, NMR spectroscopy, and the modified Mosher method. It was found that luminamicin has the 5, S, R, R, R, R, S, S, S, R, and S configurations at C2, C4, C7, C9, C10, C11, C12, C13, C16, C28, and C29, respectively. This configuration is the same as that found in nodusmicin, which has a chemical structure quite similar to luminamicin. The structure of luminamicin consists of three different rings, i.e., a decalin ring, a 10-membered macrolactone ring, and a 14-membered macrolactone ring. The resulting three-dimensional structure of luminamicin shows an interesting feature in that the maleic anhydride functionality in conjugation with the enol ether group of the 14-membered macrolactone is nearly perpendicular to the plane of the other two rings.