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Elansolid A3, a Unique p ‐Quinone Methide Antibiotic from Chitinophaga sancti
Author(s) -
Jansen Rolf,
Gerth Klaus,
Steinmetz Heinrich,
Reinecke Silke,
Kessler Wolfgang,
Kirschning Andreas,
Müller Rolf
Publication year - 2011
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.201100457
Subject(s) - polyketide , quinone methide , chemistry , antibiotics , stereochemistry , quinone , biology , biochemistry , gene , biosynthesis
Hen or egg? The polyketide‐based p ‐quinone methide antibiotic, elansolid A3, was isolated from the gliding bacterium Chitinophaga sancti. It now appears probable that elansolid A3 is the underlying biosynthetic product of the atropisomeric macrolide antibiotics elansolid A1 and A2 (see scheme). Under mild basic conditions the interconversion of elansolid isomers A1–A3 was observed. Under mild acidic conditions a Grob‐type fragmentation of elansolid A3 led to the p ‐hydroxy styryl isomer elansolid D.