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Biosynthesis of the myxobacterial antibiotic corallopyronin A

Authors :
Cristian Gurgui
Till F. Schäberle
Friederike Lohr
Jörn Piel
Mustafa El Omari
Gabriele M. König
Shwan Rachid
Alexander Schmitz
Rolf Müller
Stefan Kehraus
Özlem Erol
Source :
Chembiochem : a European journal of chemical biology. 11(9)
Publication Year :
2010

Abstract

Corallopyronin A is a myxobacterial compound with potent antibacterial activity. Feeding experiments with labelled precursors resulted in the deduction of all biosynthetic building blocks for corallopyronin A and revealed an unusual feature of this metabolite: its biosynthesis from two chains, one solely PKS-derived and the other NRPS/PKS-derived. The starter molecule is believed to be carbonic acid or its monomethyl ester. The putative corallopyronin A biosynthetic gene cluster is a trans-AT-type mixed PKS/NRPS gene cluster, containing a beta-branching cassette. Striking features of this gene cluster are a NRPS-like adenylation domain that is part of a PKS-type module and is believed to be responsible for glycine incorporation, as well as split modules with individual domains occurring on different genes. It is suggested that CorB is a trans-acting ketosynthase and it is proposed that it catalyses the Claisen condensation responsible for the interconnection of the two chains. Additionally, the stereochemistry of corallopyronin A was deduced by a combination of a modified Mosher's method and ozonolysis with subsequent chiral GC analyses.

Details

ISSN :
14397633
Volume :
11
Issue :
9
Database :
OpenAIRE
Journal :
Chembiochem : a European journal of chemical biology
Accession number :
edsair.doi.dedup.....53a85ee8788df3e507faf968935005d1