Catalytic site-selective thiocarbonylations and deoxygenations of vancomycin reveal hydroxyl-dependent conformational effects.
Catalytic site-selective thiocarbonylations and deoxygenations of vancomycin reveal hydroxyl-dependent conformational effects.
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DOI：
10.1021/ja302692j
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发表时间：
2012-06-13
影响因子：
15
通讯作者：
Miller, Scott J.
中科院分区：
文献类型：
--
作者：
Fowler, Brandon S.;Laemmerhold, Kai M.;Miller, Scott J.
我们研究了基于多肽的催化剂，用于万古霉素保护形式的位点选择性硫代羰基化。确定了几种催化剂增强或改变了底物所表现出的固有选择性。两种催化剂，一种通过筛选确定，另一种通过合理设计，证明了在0.50克尺度上有效。脱氧最终产生了两个新的脱氧万古霉素衍生物，其中一个新化合物的脱氧结果令人惊讶。这些效应反映在新的类似物的生物活性中，并支持某些羟基在天然结构中的结构作用。
We have examined peptide-based catalysts for the site-selective thiocarbonylation of a protected form of vancomycin. Several catalysts were identified that either enhanced or altered the inherent selectivity profile exhibited by the substrate. Two catalysts, one identified through screening, and another through rational design, were demonstrated to be effective on 0.50-gram scale. Deoxygenations led ultimately to two new deoxy-vancomycin derivatives, and surprising conformational consequences of deoxygenation were revealed for one of the new compounds. These effects were mirrored in the biological activities of the new analogs, and support a structural role for certain hydroxyls in the native structure.
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影响因子：
2.1
作者：
Griswold, KS;Miller, SJ
通讯作者：
Miller, SJ
DOI：
10.1039/p29910001481
发表时间：
1991-10-01
期刊：
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2
影响因子：
--
作者：
EVERETT, JR;HUNT, E;TYLER, JW
通讯作者：
TYLER, JW
影响因子：
1.8
作者：
GUIBE, F;DANGLES, O;BALAVOINE, G
通讯作者：
BALAVOINE, G
影响因子：
2.7
作者：
Boger, DL;Loiseleur, O;Wu, JH
通讯作者：
Wu, JH
影响因子：
21.8
作者：
Fiori, Kristin Williams;Puchlopek, Angela L. A.;Miller, Scott J.
通讯作者：
Miller, Scott J.