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Université de Fribourg

Proline as a charge stabilizing amino acid in peptide radical cations

Monney, Nicolas P.-A. ; Bally, Thomas ; Giese, Bernd

In: Journal of Physical Organic Chemistry, 2015, vol. 28, no. 5, p. 347–353

Long distance electron transfer in proteins requires relay stations that can be transitorily oxidized or reduced. Although individual prolines cannot assume this function, because of their high ionization energy, it has been shown that polyprolines have the ability to transfer charges. In order to determine the role of the proline in the hole distribution and transport within a PheProPhe...

Université de Fribourg

Regioselective oxidative ring opening of cyclopropyl silyl ethers: a quantum chemical study

Rinderhagen, Heiko ; Mattay, Jochen ; Nussbaum, Rafael ; Bally, Thomas

In: Chemistry, a European Journal, 2010, vol. 16, no. 24, p. 7121–7124

In contrast to the structurally and configurationally stable alkyl- or aryl-substituted cyclopropyl radical cations, cyclopropyl silyl ethers undergo spontaneous ring opening upon oxidation whereby the endocyclic C-C(O-TMS) bond is cleaved with remarkable selectivity. DFT calculations on 1-trimethylsilyloxybicyclo[4.1.0]heptane show that this selectivity arises from the topology of the potential...