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Issue 12, 2015
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Promiscuous indolyl vinyl isonitrile synthases in the biogenesis and diversification of hapalindole-type alkaloids

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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 1a. This approach allows the preparatively useful generation of a series of antibiotics with increased lipophilicity over that of the parent antibiotic.

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

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Publication details

The article was received on 07 Aug 2015, accepted on 03 Oct 2015 and first published on 06 Oct 2015


Article type: Edge Article
DOI: 10.1039/C5SC02919H
Chem. Sci., 2015,6, 6836-6840
  • Open access: Creative Commons BY-NC license
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    Promiscuous indolyl vinyl isonitrile synthases in the biogenesis and diversification of hapalindole-type alkaloids

    K. Ittiamornkul, Q. Zhu, D. S. Gkotsi, D. R. M. Smith, M. L. Hillwig, N. Nightingale, R. J. M. Goss and X. Liu, Chem. Sci., 2015, 6, 6836
    DOI: 10.1039/C5SC02919H

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