Skip to content

Research at St Andrews

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

Research output: Contribution to journalArticle


Open Access permissions



M. J. Corr, S. V. Sharma, C. Pubill Ulldemolins, R. T. Bown, P. Poirot, D. R. M. Smith, C. Cartmell, A. Abou Fayad, R. J. M Goss

School/Research organisations


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.


Original languageEnglish
Pages (from-to)2039-2046
Number of pages8
JournalChemical Science
Issue number3
Early online date11 Nov 2016
StatePublished - 1 Mar 2017
Scopus citations1

Discover related content
Find related publications, people, projects and more using interactive charts.

View graph of relations

Related by author

  1. A one-pot synthesis of symmetrical and unsymmetrical dipeptide ureas

    Abou Fayad, A., Pubill Ulldemolins, C., Sharma, S. V., Day, D. & Goss, R. J. M. Sep 2015 In : European Journal of Organic Chemistry. 25, p. 5603-5609 8 p.

    Research output: Contribution to journalArticle

  2. Mild, aqueous α-arylation of ketones: towards new diversification tools for halogenated metabolites and drug molecules

    Marelli, E., Renault, Y., Sharma, S. V., Nolan, S. P. & Goss, R. J. M. 17 Mar 2017 In : Chemistry - A European Journal. 23, 16, p. 3832-3836 5 p.

    Research output: Contribution to journalArticle

  3. Rapid enzyme regeneration results in the striking catalytic longevity of an engineered, single species, biocatalytic biofilm

    Tong, X., Barberi, T. T., Botting, C. H., Sharma, S. V., Simmons, M. J. H., Overton, T. W. & Goss, R. J. M. 21 Oct 2016 In : Microbial Cell Factories. 15, 1, 11 p., 180

    Research output: Contribution to journalArticle

  4. An unusual flavin-dependent halogenase from the metagenome of the marine sponge Theonella swinhoei WA

    Smith, D. R. M., Uria, A. R., Helfrich, E. J. N., Milbredt, D., van Pée, K-H., Piel, J. & Goss, R. J. M. 19 May 2017 In : ACS Chemical Biology. 12, 5, p. 1281-1287 7 p.

    Research output: Contribution to journalArticle

  5. One-pot access to L-5,6-dihalotryptophans and L-alknyltryptophans using tryptophan synthase

    Corr, M. J., Smith, D. R. M. & Goss, R. J. M. 17 Nov 2016 In : Tetrahedron. 72, 46, p. 7306-7310 5 p.

    Research output: Contribution to journalArticle

Related by journal

  1. pH controlled assembly of a self-complementary halogen-bonded dimer

    Maugeri, L., Jamieson, E., Cordes, D. B., Slawin, A. M. Z. & Philp, D. 1 Feb 2017 In : Chemical Science. 8, 2, p. 938-945

    Research output: Contribution to journalArticle

  2. Non-bonding 1,5-S•••O interactions govern chemo- and enantioselectivity in isothiourea-catalyzed annulations of benzazoles

    Robinson, E. R. T., Walden, D. M., Fallan, C., Greenhalgh, M. D., Cheong, P. H-Y. & Smith, A. D. 1 Dec 2016 In : Chemical Science. 7, 12, p. 6919-6927 9 p.

    Research output: Contribution to journalArticle

  3. Circulatory zinc transport is controlled by distinct interdomain sites on mammalian albumins

    Handing, K. B., Shabalin, I. G., Kassaar, O., Khazaipoul, S., Blindauer, C. A., Stewart, A. J., Chruszcz, M. & Minor, W. 1 Nov 2016 In : Chemical Science. 7, 11, p. 6635-6648 14 p.

    Research output: Contribution to journalArticle

  4. Electronic nature of zwitterionic alkali metal methanides, silanides and germanides - a combined experimental and computational approach

    Li, H., Aquino, A. J. A., Cordes, D. B., Hase, W. L. & Krempner, C. 7 Oct 2016 In : Chemical Science. Advance Article

    Research output: Contribution to journalArticle

ID: 247543679