All Outputs (2)

Unusually high α-proton acidity of prolyl residues in cyclic peptides (2020)
Journal Article
Maguire, O. R., Taylor, B., Higgins, E. M., Rees, M., Cobb, S. L., Simpkins, N. S., …O'Donoghue, A. C. (2020). Unusually high α-proton acidity of prolyl residues in cyclic peptides. Chemical Science, 11(29), 7722-7729. https://doi.org/10.1039/d0sc02508a

The acidity of the α-proton in peptides has an essential role in numerous biochemical reactions and underpins their stereochemical integrity, which is critical to their biological function. We report a detailed kinetic and computational study of the... Read More about Unusually high α-proton acidity of prolyl residues in cyclic peptides.

The Impact of Macrocycle Conformation on the Taxadiene-Forming Carbocation Cascade: Insight Gained from Sobralene, a Recently Discovered Verticillene Isomer (2020)
Journal Article
Hayes, C. J., Palframan, M. J., & Pattenden, G. (2020). The Impact of Macrocycle Conformation on the Taxadiene-Forming Carbocation Cascade: Insight Gained from Sobralene, a Recently Discovered Verticillene Isomer. Journal of Organic Chemistry, 85(6), 4507-4514. https://doi.org/10.1021/acs.joc.0c00369

DFT calculations on the carbocation intermediates that connect the biosynthetic pathways leading to the sand fly pheromone sobralene and taxadiene have been made. Establishment of the conformation of the macrocyclic carbocation intermediate required... Read More about The Impact of Macrocycle Conformation on the Taxadiene-Forming Carbocation Cascade: Insight Gained from Sobralene, a Recently Discovered Verticillene Isomer.