Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 15, Issue 19, Pages 4081-4085Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c7ob00295e
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Funding
- European Commission, Seventh Framework Programme (FLUOR21, ITN, Gimenez)
- Engineering and Physical Sciences Research Council (EPSRC) [EP/J015989/1]
- EPSRC [EP/J015989/1] Funding Source: UKRI
- Engineering and Physical Sciences Research Council [EP/J015989/1] Funding Source: researchfish
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The SNAr arylation of peptides with perfluoroaromatics provides a route by which to install a useful chemical handle that enables both F-19-NMR analysis and further chemical modification. However, chemo-selective arylation in peptides containing multiple nucleophilic side chains currently presents a challenge to the field. Herein, we demonstrate that employing 2,2,2-trifluoroethanol (TFE) as a solvent in peptide SNAr reactions significantly improves nucleophile-selectivity when compared to N, N'-dimethylformamide (DMF).
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