Journal article Open Access

Buchwald Hartwig diversification of unprotected halotryptophans, halotryptophan containing tripeptides and the natural product barettin in aqueous conditions

Renault, Yohann JG; Lynch, Rosemary; Marelli, Enrico; Sharma, Sunil V; Pubill-Ulldemolins, Cristina; Sharp, Joshua A; Cartmell, Christopher; Cárdenas, Paco; Goss, Rebecca JM

Blending synthetic biology and synthetic chemistry represents a powerful approach to diversity complex molecules. To further enable this, compatible synthetic tools are needed. We report the first Buchwald Hartwig amination reactions with unprotected halotryptophans under aqueous conditions and demonstrate this methodology is applicable also to the modification of unprotected tripeptides and the natural product barettin.

ACKNOWLEDGMENTS: 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 GenoChemetics (to R. J. M. G.)). P. Cárdenas received support from the European Union's Horizon 2020 research and innovation program through the SponGES project (grant agreement no. 679849). This document reflects only the authors' view and the Executive Agency for Small and Medium-sized Enterprises (EASME) is not responsible for any use that may be made of the information it contains. We thank the National Mass Spectrometry service at Swansea for MS characterisation of synthetic products. COPYRIGHT: This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. The journal Chemistry Communications is © The Royal Society of Chemistry 2019. SUPPLEMENTARY INFORMATION: Electronic supplementary information (ESI) available: Experimental procedures; NMR characterisation; LC-MS characterisation. See DOI: 10.1039/ c9cc02554e
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