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Promiscuous indolyl vinyl isonitrile synthases in the biogenesis and diversification of hapalindole-type alkaloids

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Date
2015
Author
Ittiamornkul, Kuljira
Zhu, Qin
Gkotsi, Danai Stella
Smith, Duncan Robert Miller
Hillwig, Matthew
Nightingale, Nicole
Goss, Rebecca Jane Miriam
Liu, Xinyu
Funder
European Research Council
Grant ID
GCGXC
Keywords
QD Chemistry
NDAS
Metadata
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Abstract
The hapalindole-type alkaloids naturally show striking late stage diversification of what was believed to be a conserved intermediate, cis-indolyl vinyl isonitrile (1a). Here we demonstrate enzymatically, as well as through applying a synthetic biology approach, that the pathway generating 1a (itself, a potent natural broad‐spectrum antibiotic) is also dramatically flexible. We harness this to enable early stage diversification of the natural product and generation of a wide range of halo-analogues of cis-indolyl vinyl isonitrile. This approach allows the preparatively useful generation of a series of antibiotics with increased lipophilicity over that of the parent antibiotic.
Citation
Ittiamornkul , K , Zhu , Q , Gkotsi , D S , Smith , D R M , Hillwig , M , Nightingale , N , Goss , R J M & Liu , X 2015 , ' Promiscuous indolyl vinyl isonitrile synthases in the biogenesis and diversification of hapalindole-type alkaloids ' , Chemical Science , vol. In press . https://doi.org/10.1039/C5SC02919H
Publication
Chemical Science
Status
Peer reviewed
DOI
https://doi.org/10.1039/C5SC02919H
ISSN
2041-6520
Type
Journal article
Rights
Copyright 2015 the Authors. This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence (http://creativecommons.org/licenses/by-nc/3.0/).
Description
The research leading to these results has received funding from the Department of Chemistry, University of Pittsburgh (to X.L) and the European Research Council under the European Union’s Seventh Framework Programme (FP7/2007-2013/ERC grant agreement no 614779 (to R.J.M.G).
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  • University of St Andrews Research
URL
http://www.rsc.org/suppdata/c5/sc/c5sc02919h/c5sc02919h1.pdf
URI
http://hdl.handle.net/10023/7655

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