Publications by authors named "Matteo Pollastrini"

2 Publications

  • Page 1 of 1

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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http://dx.doi.org/10.1021/acs.joc.1c00184DOI Listing
June 2021

Light-mediated control of activity in a photosensitive foldamer that mimics an esterase.

Chem Commun (Camb) 2021 Mar;57(18):2269-2272

Department of Chemical Sciences, University of Padova, Padova 35131, Italy.

We report a catalytic foldamer in which a fumaramide chromophore links a Ser residue to a helical domain that contains within its sequence the residues His and Asp. Photoisomerization of the fumaramide chromophore (with E geometry) to the corresponding maleamide (with Z geometry) brings together a 'catalytic triad' of Ser, His, and Asp, triggering esterase activity that is absent in the fumaramide isomer. The fumaramide/maleamide linker thus acts as a light-sensitive switchable cofactor for activation of catalytic activity in short foldamers.
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http://dx.doi.org/10.1039/d0cc08309gDOI Listing
March 2021