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Abstract
A thorough experimental and computational study on the conformational properties of (S)-indoline-2-carboxylic acid derivatives has been conducted. Methyl (S)-1-acetylindoline-2-carboxylate, both a mimetic of proline and phenylalanine, shows a remarkable tendency toward the cis amide isomer when dissolved in polar solvents. This behavior is opposite to the general preference of proline for the trans isomer, making indoline-2-carboxylic acid a good candidate for the design of different secondary structures and new materials.
Highlights
Conformational diversity is Nature’s way of disclosing important properties; a deeper understanding of the intrinsic conformational order of natural and unnatural amino acids is essential for the rational design of biomimetic compounds
They recently developed new soft materials based on L-DOPA,[36,37] a psychoactive analogue of phenylalanine, and in collaboration with them we could spot through chiroptical techniques the elusive π-helix motif attained by oligomers containing pyroglutamic acid,[38] a proline mimetic. (S)-Indoline-2-carboxylic acid ((2S)-Ind) is an interesting case, as it is both a mimetic of L-proline and L-phenylalanine. (2S)-Ind can be considered as the result of the fusion of an aromatic ring to the pyrrolidine bond between C4 and C5 of proline
Lattice relaxation time T1 of the two species (T1cis = 2.39 s; T1trans = 2.46 s) we found the approach outlined by Perrin and Dwyer to be convenient.60 2D exchange spectroscopy (EXSY), which provides a map of the exchanging species, was used
Summary
Solvent-Dependent Amide Bond Isomerization of (S)‐Indoline-2-carboxylic Acid Derivatives. Downloaded via 154.13.228.108 on March 2, 2022 at 20:54:13 (UTC). See https://pubs.acs.org/sharingguidelines for options on how to legitimately share published articles
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