Abstract
The peptide protons in N-acetyl-α,-dehydrodipeptides (DHDP) dissociate in aqueous methanol in the presence of magnesium salts upon the addition of alkali, which favors the diastereoselectivities of their hydrogenation over Pd/C. By contrast, the N—H bonds of the N-acetyl groups in DHDP seem not to dissociate under these conditions. The dissociation of the peptide N—H bonds in strongly alkaline solutions was studied by 19F NMR spectroscopy for model compounds containing the 4-FC6H4 fragment.
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Lisichkina, I.N., Ivanova, A.G., Peregudov, A.S. et al. Deprotonation of the peptide NH groups and diastereoselective hydrogenation of N-acetyl-α,-dehydrodipeptides. Russian Chemical Bulletin 50, 738–739 (2001). https://doi.org/10.1023/A:1011397803696
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DOI: https://doi.org/10.1023/A:1011397803696