Divergent unprotected peptide macrocyclisation by palladium-mediated cysteine arylation

Anthony J. Rojas, Chi Zhang, Ekaterina V. Vinogradova, Nathan H. Buchwald, John Reilly, Bradley L. Pentelute, Stephen L. Buchwald

Chemical Science · 2017 · 113 citations · 27 references

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Abstract

+ 7 positions, respectively, were cyclised to introduce a diverse array of aryl and bi-aryl linkers. These two series of macrocyclic peptides displayed similar linker-dependent lipophilicity, phospholipid affinity, and unique volume of distributions. Additionally, one of the bioactive peptides showed target binding affinity that was predominantly affected by the length of the linker. Collectively, this divergent strategy allowed rapid and convenient access to various aryl linkers, enabling the systematic evaluation of the effect of appending unit on the medicinal properties of macrocyclic peptides.

References

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