Browse by author
Lookup NU author(s): Professor Paul RaceORCiD
Full text for this publication is not currently held within this repository. Alternative links are provided below where available.
© 2017 The Royal Society of Chemistry. Kalimantacin A and batumin exhibit potent and selective antibiotic activity against Staphylococcus species including MRSA. Both compounds are formed via a hybrid polyketide synthase/non-ribosomal peptide synthetase (PKS-NRPS) biosynthetic pathway and from comparison of the gene clusters it is apparent that batumin from Pseudomonas batumici and kalimantacin from P. fluorescens are the same compound. The linear structure of this unsaturated acid was assigned by spectroscopic methods, but the relative and absolute stereochemistry of the five stereocentres remained unknown. Herein we describe isolation of kalimantacin A and two further metabolites 17,19-diol 2 and 27-descarbomyl hydroxyketone 3 from cultures of P. fluorescens. Their absolute and relative stereochemistries are rigorously determined using a multidisciplinary approach combining natural product degradation and fragment synthesis with bioinformatics and NMR spectroscopy. Diol 2 has the 5R, 15S, 17S, 19R, 26R, 27R configuration and is the immediate biosynthetic precursor of the bioactive kalimantacin A formed by oxidation of the 17-alcohol to the ketone.
Author(s): Thistlethwaite IRG, Bull FM, Cui C, Walker PD, Gao S-S, Wang L, Song Z, Masschelein J, Lavigne R, Crump MP, Race PR, Simpson TJ, Willis CL
Publication type: Article
Publication status: Published
Journal: Chemical Science
Year: 2017
Volume: 8
Issue: 9
Pages: 6196-6201
Print publication date: 01/09/2017
Online publication date: 11/07/2017
Acceptance date: 02/07/2017
ISSN (print): 2041-6520
ISSN (electronic): 2041-6539
Publisher: Royal Society of Chemistry
URL: https://doi.org/10.1039/c7sc01670k
DOI: 10.1039/c7sc01670k
Altmetrics provided by Altmetric
