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Sonogashira diversification of unprotected halotryptophans, halotryptophan containing tripeptides; and generation of a new to nature bromo-natural product and its diversification in water

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Date
01/03/2017
Author
Corr, M. J.
Sharma, S. V.
Pubill Ulldemolins, C.
Bown, R. T.
Poirot, P.
Smith, D. R. M.
Cartmell, C.
Abou Fayad, A.
Goss, R. J. M
Funder
European Research Council
European Commission
Grant ID
GCGXC
659399
Keywords
QD Chemistry
NDAS
BDC
Metadata
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Abstract
The blending together of synthetic chemistry with natural product biosynthesis represents a potentially powerful approach to synthesis; to enable this, further synthetic tools and methodologies are needed. To this end, we have explored the first Sonogashira cross-coupling to halotryptophans in water. Broad reaction scope is demonstrated and we have explored the limits of the scope of the reaction. We have demonstrated this methodology to work excellently in the modification of model tripeptides. Furthermore, through precursor directed biosynthesis, we have generated for the first time a new to nature brominated natural product bromo-cystargamide, and demonstrated the applicability of our reaction conditions to modify this novel metabolite.
Citation
Corr , M J , Sharma , S V , Pubill Ulldemolins , C , Bown , R T , Poirot , P , Smith , D R M , Cartmell , C , Abou Fayad , A & Goss , R J M 2017 , ' Sonogashira diversification of unprotected halotryptophans, halotryptophan containing tripeptides; and generation of a new to nature bromo-natural product and its diversification in water ' , Chemical Science , vol. 8 , no. 3 , pp. 2039-2046 . https://doi.org/10.1039/C6SC04423A
Publication
Chemical Science
Status
Peer reviewed
DOI
https://doi.org/10.1039/C6SC04423A
ISSN
2041-6520
Type
Journal article
Rights
Copyright 2016 the Authors. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
Description
The research leading to these results has received funding from 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), and ERAIB (Grant no. 031A338A)) (to R.J.M.G), and H2020-MSCA-IF-2014 (Grant no. 659399 (to C.P.U). We thank EPSRC National Mass Spectrometry Service Centre (Swansea, UK) for assistance in acquiring MS analysis on a number of the lower molecular weight tryptophan derivatives.
Collections
  • University of St Andrews Research
URI
http://hdl.handle.net/10023/9944

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