Pellasoren: Structure Elucidation, Biosynthesis, and Total Synthesis of a Cytotoxic Secondary Metabolite from Sorangium cellulosum

被引:51
|
作者
Jahns, Christine [1 ,2 ]
Hoffmann, Thomas [3 ]
Mueller, Stefan [3 ]
Gerth, Klaus [2 ]
Washausen, Peter [2 ]
Hoefle, Gerhard [2 ]
Reichenbach, Hans [2 ]
Kalesse, Markus [1 ,2 ]
Mueller, Rolf [3 ]
机构
[1] Leibniz Univ Hannover, Inst Organ Chem, D-30167 Hannover, Germany
[2] HZI, Braunschweig, Germany
[3] Univ Saarland, Helmholtz Zentrum Infekt Forsch & Pharmazeut Biot, HIPS, D-66123 Saarbrucken, Germany
关键词
biosynthesis; myxobacteria; natural products; Sorangium cellulosum; total synthesis; MODULAR POLYKETIDE SYNTHASES; ANSAMITOCIN; PREDICTION; SUBSTRATE; GENES; ALDOL; UNITS;
D O I
10.1002/anie.201200327
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Genetic analysis of biosynthetic gene clusters is becoming an accepted tool to predict the stereochemical outcome of a biosynthesis. However, in the case of pellasoren, one chiral center was not predicted correctly. The absolute configuration was verified by total synthesis, which also demonstrated that stereoselective protonations can be successfully applied to natural products synthesis. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:5239 / 5243
页数:5
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