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Sulfangolids, Macrolide Sulfate Esters from Sorangium cellulosum
Author(s) -
Zander Wiebke,
Irschik Herbert,
Augustiniak Hermann,
Herrmann Martina,
Jansen Rolf,
Steinmetz Heinrich,
Gerth Klaus,
Kessler Wolfgang,
Kalesse Markus,
Höfle Gerhard,
Müller Rolf
Publication year - 2012
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201100851
Subject(s) - myxobacteria , sulfate , chemistry , stereochemistry , conjugated system , biosynthesis , biochemistry , organic chemistry , biology , bacteria , gene , genetics , polymer
Sulfangolids are the first sulfate ester containing secondary metabolites from myxobacteria. The metabolites 1 – 4 and the structurally related kulkenon ( 5 ) were isolated from different strains of the species Sorangium cellulosum . In the course of isolation all metabolites proved to be rather sensitive due to their conjugated double bond systems and the strong acidic nature of the sulfate ester in sulfangolids. The relative configuration of sulfangolid C ( 3 ) was assigned by extensive 1D and 2D NMR analysis and molecular modelling. In addition, the biosynthesis of 3 was studied by feeding experiments.