A Unique and Stable Polyproline I Helix Sorted out from Conformational Equilibrium by Solvent Polarity

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dc.contributor.authorPollastrini, Matteo
dc.contributor.authorPasquinelli, Luca
dc.contributor.authorGórecki, Marcin
dc.contributor.authorBalzano, Federica
dc.contributor.authorCupellini, Lorenzo
dc.contributor.authorLipparini, Filippo
dc.contributor.authorBarretta, Gloria Uccello
dc.contributor.authorMarchetti, Fabio
dc.contributor.authorPescitelli, Gennaro
dc.contributor.authorAngelici, Gaetano
dc.contributor.organizationInstitute of Organic Chemistry, Polish Academy of Sciencesen
dc.contributor.organizationDipartimento di Chimica e Chimica Industriale, Universitàdi Pisaen
dc.date.accessioned2022-10-26T14:08:49Z
dc.date.available2022-10-26T14:08:49Z
dc.date.issued2022
dc.description.abstractPolyproline I helical structures are often considered as the hidden face of their most famous geminal sibling, Polyproline II, as PPI is generally spotted only within a conformational equilibrium. We designed and synthesized a stable Polyproline I structure exploiting the striking tendency of (S)-indoline-2-carboxylic acid to drive the peptide bond conformation toward the cis amide isomer, when dissolved in polar solvents. The cooperative effect of only four amino acidic units is sufficient to form a preferential structure in solution. We shed light on this rare secondary structure with a thorough analysis of the spectroscopic and chiroptical properties of the tetramer, supported by X-ray crystallography and computational studies.en
dc.description.sponsorshipUniversity of Pisa (PRA 2018_23, PRA_2020_27, and PRA 2020_77)
dc.identifier.citationhttps://doi.org/10.1021/acs.joc.2c01377en
dc.identifier.doi10.1021/acs.joc.2c01377
dc.identifier.issn0022-3263
dc.identifier.issn1520-6904
dc.identifier.urihttps://open.icm.edu.pl/handle/123456789/21795
dc.language.isoen
dc.publisherAmerican Chemical Societyen
dc.rightsUznanie autorstwa 4.0 Międzynarodowe*
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/*
dc.subjectcircular dichroism spectroscopyen
dc.subjectconformationen
dc.subjectmolecular structureen
dc.subjectoligomersen
dc.subjectsolventsen
dc.titleA Unique and Stable Polyproline I Helix Sorted out from Conformational Equilibrium by Solvent Polarityen
dc.typearticleen
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