Fig. 3: Mechanistic studies. | Nature Communications

Fig. 3: Mechanistic studies.

From: Radiolabeling of oligopeptides by selective hydrogen isotope exchange with deuterium and tritium in aqueous buffers

Fig. 3: Mechanistic studies.

A initial scope of deuteration with functionalized hydrocarbons and amino acids (blue dot = deuterium). Conditions: 0.02 mmol substrate, 2.5 mol% [Ir(COD)Cl]2, 5 mol% ligand L11, Borax/HCl buffer pH 9, 90 °C, 1 h when not indicated otherwise. Deuterium content analyzed by 1H-NMR when not indicated otherwise. Yield obtained with quantitative NMR. a) deuterium content analyzed by LC-MS; b) conditions for l-Arg: 0.02 mmol substrate, 5 mol% [Ir(COD)Cl]2, 10 mol% ligand L11, Borax/HCl buffer pH 9, 90 °C, 17 h; (B) DFT calculations for the pathways leading to the active species formation. Reaction free energies ΔGr (kcal/mol) are given above the corresponding reaction arrows, most energetically favorable pathways are represented with thick arrows.

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