ChemSci2017.pdf (563.16 kB)
Sonogashira diversification of unprotected halotryptophans, halotryptophan containing tripeptides; and generation of a new to nature bromo-natural product and its diversification in water
journal contribution
posted on 2023-06-09, 15:45 authored by M J Corr, S V Sharma, Cristina Pubill Ulldemolins, R T Bown, P Poirot, D R M Smith, C Cartmell, A Abou Fayad, R J M GossThe 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.
History
Publication status
- Published
File Version
- Published version
Journal
Chemical ScienceISSN
2041-6520Publisher
Royal Society of ChemistryExternal DOI
Issue
3Volume
8Page range
2039-2046Department affiliated with
- Chemistry Publications
Full text available
- Yes
Peer reviewed?
- Yes
Legacy Posted Date
2018-11-09First Open Access (FOA) Date
2018-11-09First Compliant Deposit (FCD) Date
2018-11-09Usage metrics
Categories
No categories selectedKeywords
Licence
Exports
RefWorks
BibTeX
Ref. manager
Endnote
DataCite
NLM
DC