PH-Dependent Conformational Switching of Amide Bonds from Full trans to Full cis and Vice Versa

Thurston R, Zantop V, Park KS, Maid H, Seitz A, Heinrich M (2022)

Publication Type: Journal article

Publication year: 2022

Journal

Organic Letters American Chemical Society

DOI: 10.1021/acs.orglett.2c00938

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.

Authors with CRIS profile

Ryan Thurston Professur für Pharmazeutische Chemie Anke Seitz Lehrstuhl für Pharmazeutische Chemie Markus Heinrich Professur für Pharmazeutische Chemie

How to cite

APA:

Thurston, R., Zantop, V., Park, K.S., Maid, H., Seitz, A., & Heinrich, M. (2022). PH-Dependent Conformational Switching of Amide Bonds from Full trans to Full cis and Vice Versa. Organic Letters. https://dx.doi.org/10.1021/acs.orglett.2c00938

MLA:

Thurston, Ryan, et al. "PH-Dependent Conformational Switching of Amide Bonds from Full trans to Full cis and Vice Versa." Organic Letters (2022).

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