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pH-Dependent Conformational Switching of Amide Bonds─from Full trans to Full cis and Vice Versa.

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Strategies enabling the pH-dependent conformational switching of amide bonds from trans to cis, and vice versa, are yet limited in the sense that, in a suitable pH range, one rotamer… Click to show full abstract

Strategies enabling the pH-dependent conformational switching of amide bonds from trans to cis, and vice versa, are yet limited in the sense that, in a suitable pH range, one rotamer may be stabilized to a large extent while the complementary pH range only leads to a mixture of isomers. By exploiting the effects of steric demand and the interaction of the amide carbonyl with a positive charge, we herein present the first examples for reversible pH-dependent switching from full trans to full cis.

Keywords: switching amide; cis vice; amide bonds; dependent conformational; vice versa; conformational switching

Journal Title: Organic letters
Year Published: 2022

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