The attraction of H-bonding: Proline derivatives with a C4-endo ring pucker and a preference for the trans amide conformer are introduced as building blocks to tune the cis/trans amide conformer ratio in Xaa-Pro bonds within peptides. Noncovalent interactions, such as hydrogen bonding between the substituent at C4 of the proline ring and the amide backbone are key for favoring or disfavoring the trans conformer (see picture).
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Kuemin et al. (2010) studied this question.
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