Publications by authors named "Luca Pasquinelli"

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A Proline Mimetic for the Design of New Stable Secondary Structures: Solvent-Dependent Amide Bond Isomerization of ()-Indoline-2-carboxylic Acid Derivatives.

J Org Chem 2021 06 3;86(12):7946-7954. Epub 2021 Jun 3.

Dipartimento di Chimica e Chimica Industriale, Università di Pisa, Via G. Moruzzi 13, 56124 Pisa, Italy.

A thorough experimental and computational study on the conformational properties of ()-indoline-2-carboxylic acid derivatives has been conducted. Methyl ()-1-acetylindoline-2-carboxylate, both a mimetic of proline and phenylalanine, shows a remarkable tendency toward the amide isomer when dissolved in polar solvents. This behavior is opposite to the general preference of proline for the isomer, making indoline-2-carboxylic acid a good candidate for the design of different secondary structures and new materials.
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June 2021